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In recent years, the development of combination therapies with immune checkpoint inhibitors (ICIs) and cytotoxic anticancer drugs has radically changed the management of diverse malignancies and significantly improved patient outcomes. Several clinical trials have shown that skin rash caused by combination therapy with ICIs and cytotoxic drugs may be more frequent and severe than that developing after administration of ICIs alone or cytotoxic drug monotherapy. However, most reports provide little information on severity, treatment, post-diagnosis course, and recurrence of rashes on drug rechallenges. We aimed to describe the experience of skin rashes developing within 2 weeks from the first administration of combination therapy with ICIs and cytotoxic drugs in 11 patients visiting our dermatology department. This study included seven men and four women, and the patients' median age was 52 years. The primary disease was non-small-cell lung cancer in eight patients, cervical cancer in two patients, and esophageal cancer in one patient. Nine patients had a maculopapular rash and two patients developed erythema multiforme-like eruptions. The skin rash was often accompanied by extracutaneous symptoms, such as fever (n = 9), mucositis (n = 4), and liver dysfunction (n = 2). In all cases, the symptoms improved with topical steroid therapy alone, with no patients exhibiting severe symptoms requiring systemic steroids or immunosuppressive agents. In addition, when the causative drugs were re-administered after recovery from the rash, only two patients relapsed with accompanying systemic symptoms, and all patients except one were able to continue treatment using the same drug regimen. Although it was suggested that the rash caused by the combination therapy of ICIs and cytotoxic drugs may be more prominent than that caused by each agent alone, comprehensive judgment, including histopathological examination, may indicate the feasibility of continuing the treatment regimen for cancer.

Cysts of the skin are observed frequently and their diagnoses are generally straightforward. However, atypical cystic lesions for which differentiation is indistinct have been noted.We examined five cases of trichilemmal cyst with proteinaceous material (TCPM), which required differentiation from sweat duct/gland tumors. We investigated the histopathological findings of TCPMs and evaluated the immunohistochemical expression of cytokeratin (CK) 10, CK13, CK17, CK19, CD8, and CD117. Immunohistochemical analysis was performed on the 5 TCPMs, 10 trichilemmal cysts (TCs), 5 clear-cell hidradenomas, 5 poroid hidradenomas, and cutaneous normal adnexa.Apoptotic cells were present in the cyst wall with a small amount of keratin or calcification in the cavity of TCPMs. The TCPMs and TCs were negative for CK19 and CD117, on the other hand clear-cell hidradenoma and poroid hidradenoma were positive for CK19 and CD117. The restricted positivity for CK10 was detected in the suprabasal layers of the cyst walls of TCPMs and TCs. The immunostaining patterns of TCPMs and TCs were similar to those of normal follicular isthmus.The histopathological findings with characteristics of TCs and a panel of immunohistochemical antibodies including CD117, CK19, and CK10 contributed to a correct diagnosis of TCPM.

Radiation dermatitis, limited to the irradiated site, is the most common cutaneous adverse reaction due to radiotherapy. There are scattered reports of erythema multiforme-like rash, Stevens-Johnson syndrome, and toxic epidermal necrolysis associated with radiotherapy. Some of these reports include cases without remarkable drug history, which suggests rashes induced by radiotherapy. The lack of a large cohort study, however, makes it difficult to ascertain the time course, severity, and outcome of the cases. We aimed to evaluate the potential association between radiotherapy and erythema multiforme-like rash in a larger sample of patients. We examined the records of patients at our institute who received radiotherapy and developed a rash from 2010 to 2021. We present 30 patients with erythema multiforme-like rash, which arose during or after radiotherapy. We describe the background, details of radiotherapy, and clinical course of the patients including the cutaneous and extracutaneous symptoms. Radiotherapy was the most likely cause of rash, and in most cases, the rash was relieved by conservative management and radiation could be continued. When erythema multiforme-like rash arises in patients under cancer treatment, radiotherapy should be considered a potential trigger.

Lipomatous metaplasia has been rarely reported in both neoplastic and inflammatory dermatological disorders. Most neoplastic cases show the lipomatous change within the tumor silhouette, but band-like lipomatous metaplasia in the dermis under tumors has not been well-described. The aim of this study was to reveal the characteristics and relationship of intradermal band-like lipomatous metaplasia and coexisting skin tumors. A total of 20 cases with intradermal band-like lipomatous metaplasia were retrieved from 10,992 archive cases between April 1997 and March 2020 at Hyogo Cancer Center, and subjected to a detailed clinicopathologic analysis. Nine (45%) patients had superficial variant basal cell carcinoma as a coexisting neoplasm. Eight (40%) patients had squamous cell carcinoma, 5 of which were in situ. The remaining 3 (15%) cases were invasive extramammary Paget disease. All 20 cases showed at least one of 3 signs of tumor regression, namely, partial loss of overlying neoplasia, significant inflammatory infiltrate under the tumor, and fibrosis around the tumor. We concluded that intradermal band-like lipomatous metaplasia could be seen in association with the regressing process of cutaneous superficially-spreading neoplasms.

AIMS The aim of this study was to determine the clinicopathological and genetic characteristics of axillary signet-ring cell/histiocytoid carcinoma (SRCHC) and the relationship between axillary SRCHC, eyelid SRCHC, and conventional apocrine carcinoma (AC). METHODS AND RESULTS Eleven cases of axillary SRCHC, four cases of eyelid SRCHC, eight cases of axillary AC and five cases of invasive lobular carcinoma (ILC) were retrieved. Additionally, 14 axillary and 43 eyelid SRCHC cases from the literature were reviewed. Male predominance was prominent for axillary SRCHC (24:1) and eyelid SRCHC (42:5). Axillary SRCHC formed a circumscribed plaque or nodule, unlike eyelid SRCHC. Lymph node metastasis was predominantly seen in axillary SRCHC cases (72%, 18/25), but not in eyelid SRCHC cases (19%, 9/47). Axillary SRCHC and eyelid SRCHC were histopathologically similar and showed rare tubular formations. Immunoexpression of cytokeratin 7, cytokeratin 19, mucin 1, mucin 5AC, BerEP4 and androgen receptor was seen in all tested cases of the four diseases. Oestrogen and progesterone receptors were negative in both types of SRCHC and AC, but were strongly positive in ILCs. Complete loss of E-cadherin expression was seen in approximately one-quarter of both types of SRCHC and in all ILCs. PIK3CA mutations were detected in all three sequenced cases (two axillary SRCHCs and one eyelid SRCHC). CONCLUSION The histopathological, immunohistochemical and genetic findings suggest that both types of SRCHC are phenotypic variants of AC, although there are differences in sex, macroscopic findings and the frequency of lymph node metastasis among the three. In contrast, ILC differs from the other three tumour types.

Although most cases of early cutaneous squamous cell carcinoma (CSCC) are indolent, a small subset metastasize and can be fatal. However, high-risk features of CSCC are controversial, and it is difficult to predict the biological behavior. In this study, we have tested the prognostic significance of tumor budding in CSCCs4 cm in diameter. Hematoxylin and eosin-stained sections of surgically resected CSCCs (24 metastasizing and 24 nonmetastasizing cases)4 cm in size were reviewed retrospectively. Tumor bud, defined as an isolated cancer cell or a cluster comprising5 cells, was counted at a hot spot (1.23 mm), and graded between 1 and 3; grade 1: 0 to 4 buds; grade 2: 5 to 9 buds; and grade 3: ≥10 buds. Cases with grades 2 or 3 were regarded as positive for tumor budding. We found that tumor budding was positive in 83.3% of metastasizing CSCC, and 37.5% of nonmetastasizing CSCC (P0.01). Moreover, CSCCs with grade 3 tumor budding showed worse disease-specific survival (P0.01). Regarding interobserver reproducibility, the median κ value for tumor budding was significantly higher than that for histologic differentiation (P0.01). In conclusion, tumor budding may be a valuable histologic marker for risk stratification of early CSCC in routine practice. Patients with tumor budding positive CSCC may benefit from evaluation and close follow-up for regional node metastasis.

In consideration of the development of treatment options for squamous cell carcinoma (SCC), the Japanese Skin Cancer Society issued the first guidelines of SCC in 2007 and revised them in 2015. Here, we report the English version of the 2020 edition of the Japanese SCC guidelines. The first half of this article is an overview of SCC including actinic keratosis and Bowen's disease, and the second half discusses three clinical questions: (i) treatment of actinic keratosis; (ii) determination of the resection margin of the primary lesion; and (iii) treatment of radically incurable cases, as contemporary problems encountered in treating SCC. In these evaluations, all processes were implemented according to the Grading of Recommendations, Assessment, Development, Evaluation system. Also, items of recommendation concerning each clinical question were determined by a multidisciplinary expert panel consisting of dermatologists, plastic/reconstructive surgeons, radiologists, and oncologists through a comprehensive literature search and systematic reviews.

Muir-Torre syndrome is a hereditary condition characterized by occurrence of sebaceous neoplasms or keratoacanthomas and visceral tumors. The most common mechanism for this syndrome is a constitutional defect in the mismatch repair genes. We report the case of a 67-year-old woman with a mutator L homologue 1 (MLH1) mutation. She had a history of endometrial and colorectal cancers. The patient presented with a typical keratoacanthoma on the right cheek and numerous sebaceous neoplasms on the face and trunk. Seven sebaceous adenomas and a low-grade sebaceous carcinoma were excised. Most sebaceous adenomas showed dermoscopic features such as some yellow comedo-like globules and curved vessels in creamy-white areas. Moreover, they revealed pathological features such as keratoacanthoma-like architecture and peritumoral or intratumoral lymphocytes. One of these sebaceous adenomas indicated histopathologically spontaneous regression and another was continuous with the hair follicle. Immunohistochemical staining for mismatch repair proteins revealed loss of expression for MLH1 and postmeiotic segregation increased 2 (PMS2) proteins in tumor cells nuclei in both keratoacanthoma and sebaceous adenoma. Nuclei in overhanging epithelial lips of the keratoacanthoma were also negative. These findings suggest that the type of Muir-Torre syndrome-related cutaneous tumor may have been affected by mismatch repair protein deficient sites in the pilosebaceous unit.

Adenoid cystic carcinoma (ACC) is an infiltrating carcinoma composed of 2 cell types, myoepithelial and ductoglandular epithelial cells. Although approximately 70% of ACC exhibit translocations of the MYB proto-oncogene or MYB proto-oncogene like 1 (MYBL1), expression of MYB is known to be limited in myoepithelial cells. We investigated the histopathologic and genetic characteristics of ACC in 6 primary cutaneous cases. Histopathologically, 3 cases (50%) exhibited well-demarcated nodules composed of large nests, easily misdiagnosed as polymorphous sweat gland carcinoma. Two cases (33%) harbored large cystic structures resembling spiradenoma, hidradenoma, and digital papillary adenocarcinoma. A papillary pattern was focally observed in 2 cases (33%). A melting phenomenon within the myxoid stroma was seen in one case (17%). Fluorescence in situ hybridization (FISH) revealed MYB break-apart in 3 cases (50%). A combined FISH and immunohistochemical method revealed MYB break-apart signals in both p63-positive myoepithelial and p63-negative ductoglandular epithelial cells, suggesting that both cell types constitute elements of the tumor in ACC. Moreover, we established a well-circumscribed variant of ACC and proposed 3 new patterns of cystic, papillary, and melting in addition to the 3 patterns of cribriform, tubular, and solid growth.

Malignant melanoma is known to show diverse cellular morphologies, including a histiocyte-like morphology. Therefore, many non-melanocytic proliferations or infiltrates can mimic melanoma, and be confusing especially when they coexist with a true melanoma. Herein, we report an unusual case of a melanoma in situ with an underlying sarcoidal granuloma, which mimicked dermal invasion of melanoma. This case expands insight into non-neoplastic lesions closely mimicking melanoma.

Agminated nevus refers to a clustered group of melanocytic nevi confined to a localized area of the body. It rarely involves acral skin, but recognition of acquired agminated nevus (AAN) in the acral area is clinically important because it may mimic acral lentiginous melanoma (ALM). However, acral AAN has only been described in a few case reports and its clinical characteristics remain unclear. We report three additional cases of acral AAN to further analyze the differential points between ALM. Clinical images, including those of dermoscopy, of three cases of acral AAN were reviewed. The lesions were located on the sole or lateral border of the foot. All acral AAN were flat and large in size (>20 mm in greatest dimension), and associated with asymmetry and irregular border. However, no parallel ridge pattern suggesting ALM was observed on dermoscopy. In two patients, the lesions on the sole were totally resected; microscopic evaluation of these two lesions confirmed junctional nests of banal melanocytes. AAN lesions on the sole with chronic mechanical pressure are slightly larger and more diffuse; thus, they may be more likely to be overdiagnosed as malignancy upon inspection than those in the non-acral area. Understanding the concept of the disease and careful dermoscopic evaluation leads to an accurate diagnosis.

Background Distinguishing porocarcinoma from squamous cell carcinoma (SCC) is clinically significant but can pose a diagnostic dilemma. The present study sought to confirm the diagnostic utility of CD117 immunohistochemistry in distinguishing porocarcinoma from SCC and to examine histologic, carcinoembryonic antigen (CEA) immunohistochemical and CA19-9 immunohistochemical differences between these tumors. Methods Immunostaining with anti-CD117, anti-CEA and anti-CA19-9 antibodies was performed for 22 porocarcinomas and 31 SCCs. The extent of CD117, CEA and CA19-9 staining was classified as negative (

There is some confusion regarding the classification of keratoacanthoma (KA) and related lesions that have crateriform architecture. We examined the clinical courses of 66 KA lesions and related lesions after a partial biopsy to clarify the nosological concept of KA. We histopathologically classified these lesions into five types: (i) KA at various stages (53 lesions); (ii) KA-like squamous cell carcinoma (SCC) (3 lesions); (iii) KA with malignant transformation (3 lesions); (iv) infundibular SCC (5 lesions); and (v) crateriform SCC arising from solar keratosis (2 lesions). We analyzed the clinical course in each group. The regression rate of KA was 98.1% and that of KA-like SCC/KA with malignant transformation was 33.3%. No regression was observed in either infundibular SCC or crateriform SCC arising from solar keratosis. Thus, KA is a distinct entity that should be distinguished from other types of SCC with crateriform architecture based on the high frequency of regression. The regression rate of 33.3% in KA-like SCC/KA with malignant transformation indicated that KA lesions with an SCC component still have the potential for regression. However, this result also indicated that KA is biologically unstable, and some KA tend to evolve into conventional SCC with a gradual loss of the capacity for the spontaneous regression. Infundibular SCC and crateriform SCC arising from solar keratosis are fundamentally different from KA, not only according to the histopathological findings but also based on the biological properties.

We herein report the natural course of an early/proliferative stage keratoacanthoma (KA) with infiltrating islands of cytological malignancy (case 1) and a squamous cell carcinoma (SCC) with a KA-like component (case 2), which were observed until their complete regression. The presented case 1 suggests that one of the histopathological forms of KA includes this unusual, infiltrating, non-crateriform architecture, and also indicates the possibility of complete remission in the KA associated with infiltrating islands of cytological malignancy. In the presented case 2, the peripherally-associated KA-like focus was histopathologically considered to be either a remnant of KA focus or verrucous keratosis (hyperplasia). Therefore, the complete spontaneous regression of case 2 suggests that SCC arising in KA still has the potential of spontaneous regression, or that an extremely rare event, namely, the spontaneous regression of (traditional) SCC occurred in the present case.

Background Although the precise etiology of keratoacanthoma (KA) is unknown, KA is generally assumed to differentiate toward hair follicles based on previous studies of experimental carcinogenesis. Methods We performed a comprehensive immunohistochemical study of various follicular markers in all stages of KA. A total of 67 tumors, including 16 early or proliferative stage lesions, 43 well-developed stage lesions, five regressing stage lesions and three regressed stage lesions, were subjected to the analysis. Results CK15 (clone C8/144B), CK19 and CD34 were not expressed at any stage. CK1, CK10, CK16, CK17, CK15 (clone LHK15) and calretinin showed dynamic changes in their expression in KA depending on the stage. Conclusions KA is a follicular neoplasm with infundibular/isthmic (upper segmental region of hair follicles) differentiation. It is considered that early or proliferative stage tumors show keratin-filled invaginations with infundibular differentiation and gradual isthmic differentiation. Well-developed examples of KA generally show isthmic differentiation in the whole lesions. The regressed stage KAs lose the features of this type of follicular differentiation and show epidermal characteristics. No expression of CK15 (clone C8/144B) was observed in KAs, although this finding is insufficient to completely rule out the correlation between the regression of KA and the hair follicle cycle.

Keratoacanthoma is a common epithelial lesion, but its nature is controversial. Although a distinct crateriform appearance is a hallmark of keratoacanthoma, other benign or malignant skin lesions may show a similar architecture. Moreover, as lesions diagnosed as conventional keratoacanthoma may show malignant behavior, some authors consider keratoacanthoma to be a variant of squamous cell carcinoma, whereas others consider it as a distinct self-resolving squamous proliferative lesion. The controversy seems to originate from the diverse behavior of keratoacanthoma-like epithelial lesions. However, a reproducible histopathological classification criterion has been recently proposed in the diagnosis of keratoacanthoma-like epithelial lesions, and its validity is supported by several reports that deal with the natural course or molecular aspects of these lesions. This article attempts to provide a comprehensive review on recent insights and advances in the histopathological diagnosis of keratoacanthoma or related lesions, as well as summary of related published works.

Distinguishing porocarcinoma from squamous cell carcinoma (SCC) is clinically significant but can pose a diagnostic dilemma. The present study sought to confirm the diagnostic utility of CD117 immunohistochemistry in distinguishing porocarcinoma from SCC and to examine histologic, carcinoembryonic antigen (CEA) immunohistochemical and CA19-9 immunohistochemical differences between these tumors.Immunostaining with anti-CD117, anti-CEA and anti-CA19-9 antibodies was performed for 22 porocarcinomas and 31 SCCs. The extent of CD117, CEA and CA19-9 staining was classified as negative (1%), rarely positive (1-4%), focally positive (5-29%) or diffusely positive (30-100%). CD117 staining intensity was semi-quantitatively graded as weak, moderate or strong.All (100%) porocarcinomas were positive for CD117, with mainly focal (8/22) or diffuse (11/22) and moderate (9/22) to strong (8/22) staining. In contrast, only 6 of 31 SCCs (19.4%) expressed CD117 focally, and this expression was limited to the basal layer of the tumor in four cases. CEA immunostaining highlighted the lumina of all 22 porocarcinomas; however, CEA expression was not significantly different between porocarcinomas and SCCs (100 vs. 71.0%, respectively). CA19-9 was not expressed in the lumina of 5 of 22 porocarcinomas.Along with CEA, CD117 immunohistochemistry could be helpful in distinguishing porocarcinomas from SCCs.

51歳, 男性。若年時より前頭部に黒色腫瘤が存在したが, 急激に増大したため受診。径15cm大と巨大な半球状腫瘍を呈した。エクリン汗孔癌と診断, 骨を含めた切除を行い, 術後に出現した頸部リンパ節転移に対し郭清術を施行。放射線療法を追加したが皮膚, リンパ節転移が新生, 拡大し, 化学療法も併用した。5-FU, シスプラチン併用療法で腫瘍の増大, 進展は一時抑制されたが, 薬剤変更後に再度急速となり, 全身状態悪化。初診から11ヵ月の経過で永眠された。エクリン汗孔癌の予後, 治療法につき考察した。

68歳男性。2003年5月中旬より右腎部に腫瘤を自覚し, 右鼠径部にリンパ節が腫脹してきたので2003年6月23日当科を受診した。初診時3.4×3.7cm大で弾性硬の紅褐色皮下腫瘤を呈し, 生検にてメルケル細胞癌と診断した。2003年7月30日広範囲切除, 右鼠径・外腸骨リンパ節郭清術を施行し, 右鼠径部リンパ節転移を認めたため, 術後放射線療法を追加した。その後再発転移なく経過したが, 2005年4月血清NSE値が上昇し, CT上で多発肝転移像を認めた。エトポシド・シスプラチン療法は効果なく, シクロフォスファミド・ドキソルビシン・ビンクリスチン療法が著効し, 一旦CRとなった。しかし, 10月に肝転移が再発し, 胸腔内転移も認め, アムルビシンを投与するも効果なく, 2005年12月永眠された。多発肝転移を来した症例で, 化学療法の選択に難渋した。

This report concerns two Japanese women, 54 and 53 years old, with trichoblastoma. Histopathologically, these neoplasms were mainly composed of follicular germinative cells with fibrotic stroma. One of them was a giant lesion, but the other was small. Because both lesions were located in the subcutis, we termed them subcutaneous trichoblastoma.

Effect of precipitate state of Mg2Si as well as Si content in Al–Mg2Si alloys on the reduction of a die-line defect on the surface of extruded products was investigated in industrial scale. The solid product was extruded by 1500 us ton direct extrusion press at billet temperature 460°C, ram speed 9~13 mm/s and extrusion ratio 66.5. When Si content is low and a large amount of coarsened Mg2Si is present in the alloy after homogenization at 400°C for 2 h, the extruded samples have bright smooth surface and nonbright rough surface. When a microscopic Mg2Si is present in the alloy after homogenization at 200°C for 2 h, the extruded samples have high-quality surface with only nonbright and uniform surface roughness. When Si content is high and a large amount of coarsened Mg2Si is present in the alloy after homogenization at 400°C for 2 h, the extruded samples have poor-quality surface with a tearing defect. However, when a microscop ic Mg2Si is present in the alloy, which is caused by a widely used homogenizing method or after homogenization at 200°C for 2 h, the samples extruded at ram speed 9~13 mm/s have high-quality surface with only nonbright and uniform surface roughness.

In the presence of a catalytic amount of oxovanadium(IV) complexes coordinated by 1,3-diketone-type ligands, benzene and its analogues are directly oxygenated into phenols by combined use of molecular oxygen and crotonaldehyde at room temperature.

An efficient synthesis of acid-sensitive epoxides, such as chromene oxide or epoxide of γ,δ-unsaturated alcohol, was successfully achieved by the oxygenation of corresponding olefins with the combined use of an atmospheric pressure of molecular oxygen and aldoacetal catalyzed by a cobalt(II) complex coordinated with the 1,3-diketone ligand. The reactions proceeded under mild and neutral conditions, and the desired epoxides were obtained in good yields. Neither overoxidation nor decomposition of the formed epoxide was observed under the present reaction conditions. Furthermore, various silyl enol ethers and silyl ketene acetals, acid-sensitive compounds, were also smoothly monooxygenated into the corresponding α-hydroxy ketones and α-hydroxy carboxylic acid esters, respectively.

In the presence of a catalytic amount of oxovanadium(IV) complexes coordinated with 1,3-diketone ligands, fused aromatic compounds such as naphthalenes and naphthol derivatives are smoothly oxygenated into the corresponding 1,4-naphthoquinones by combined use of molecular oxygen and crotonaldehyde under an atmospheric pressure.

In the presence of a catalytic amount of cobalt(III) complex such as tris(acetylacetonato)cobalt(III), tetrahydrofurans are oxygenated into the corresponding γ-butyrolactones under mild conditions ...

In the presence of bis(3-methyl-2,4-pentanedionato)cobalt(II) complex catalyst, various trisubstituted olefins are smoothly monooxygenated into the corresponding epoxides in high yields under neutral conditions by the combined use of molecular oxygen and propionaldehyde diethyl acetal.

New and effective aerobic oxygenation reactions of olefins catalyzed by transition-metal complexes are described. (1) By the combined use of an atmospheric pressure of molecular oxygen and secondary alcohols, various kinds of olefins are converted into the corresponding alcohols in good to high yields catalyzed by a cobalt (II) complex. (2) Effective epoxidation of a wide variety of olefins involving styrenes and α, β-unsaturated carboxamide are achieved by the combination use of aldehyde and molecular oxygen catalyzed by nickel (II), iron (III), or oxovanadium (IV) complexes under mild reaction conditions. (3) Enantioselective aerobic epoxidations of unfuctionalized olefins are demonstrated by using optically active manganese (III) complexes as catalysts. (4) In the presence of acetal of aldehyde, cobalt (II) complex catalyzed aerobic epoxidation of olefins proceeds in high yield under neutral and mild conditions.

In the presence of a catalytic amount of bis(3-methyl-2,4-pentanedionato)nickel(II) (Ni(mac)2), various glycidyl esters are converted into the corresponding glycerol monoester derivatives with molecular oxygen in good to high yields.

By combined use of molecular oxygen (oxidant) and secondary or primary alcohol (reductant) in the presence of a catalytic amount of bis(2-alkyl-1,3-diketonato)oxovanadium(IV) complexes, norbornene analogues are monooxygenated into the corresponding epoxides in good yields.

In the presence of a catalytic amount of bis(1,3-diketonato)oxovanadium(IV) complex, epoxidation of α,β-unsaturated carboxamides with molecular oxygen and an aldehyde proceeds smoothly at room temperature to give the corresponding 2,3-epoxycarboxamides in good yields.

Tris[1,3-bis(p-methoxyphenyl)-1,3-propanedionato]iron(III) (Fe(dmp)3) was found to be an excellent catalyst for oxygenation of a number of olefinic compounds including styrene analogues and olefinic alcohols into the corresponding epoxides in good to quantitative yields with combined use of molecular oxygen and an aldehyde at room temperature.

In the presence of a catalytic amount of bis[1,3-di(p-methoxyphenyl)-1,3-propanedionato]nickel(II) (=Ni(dmp)2), various olefins are smoothly monooxygenated into corresponding epoxides in good yields with combined use of molecular oxygen and primary alcohol.

The oxidation of aldehydes into the corresponding carboxylic acids using a catalytic amount of nickel(II) complex under an oxygen atmosphere at room temperature is described. Bis[1,3-di(p-methoxyphenyl)-1,3-propanedionato]nickel(II)(Ni(dmp)2) behaves as an excellent catalyst for the oxidation of aldehydes to afford the corresponding carboxylic acids in good yields.

In the presence of a catalytic amount of a bis(1,3-diketonato)nickel(II) complex, trisubstituted and exo-terminal olefins or norbornene analogues are smoothly monooxygenated into the corresponding epoxides in high to quantitative yields on treatment with aldehyde under an atmospheric pressure of oxygen at room temperature.