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A simple method for the synthesis of 2,4-diaryl-2,5-dihydro-2,2'-bifurans was developed based on the reaction of α,β-unsaturated carbonyl compounds containing a furan ring with trimethylsulfonium iodide under the conditions of the Corey–Chaykovsky reaction.

The total synthesis of dodoneine and its 6-epimer is described, using HKR of epoxide and reduction with SmI 2 reactions as key steps, respectively.

A novel variant of the Nazarov cyclization of divinyl epoxides and arylvinyl epoxides, generated in solution from the corresponding ketones and ethyl bromoacetate or trimethylsulfonium iodide is developed.

Reactions of 2-hydroxyphenylmethanones 8 with 1-chloro-1-(benzotriazol-1-yl)alkanes 9 give intermediates 10a-h , which were converted by trimethylsulfonium iodide to oxirans 11a-h. Treatment of 11a-h with LDA gave either 3-hydroxymethyl-2,3-dihydrobenzofurans or 3- hydroxymethylbenzofurans depending on substituents. Benzofurans undergo electrophilic substitution at the 2-position, and this normally precludes the direct introduction of a 3-substituent. Available methods for the preparation of 3- hydroxymethylbenzofurans 1 include (i) ring syntheses which often involve multi-step reactions, 5,7 e.g. via benzofuran-2,3-dicarboxylic acid 2; (ii) Pd-catalyzed heteroannulation of 2- iodophenols 3 with O-silyl protected alkynols, 8 or from 3-(2-bromophenoxy)acrylic ester 4; 3 (iii) cyclization of 1-(2-(2-propynyloxy)phenyl)diazonium salts 5; 9 (iv) reaction of O-silyl protected 2-ethynylphenols 6 with aldehydes under TBAF catalysis; 10 (v) oxidation of 3- methylbenzofurans 7 with selenium dioxide followed by reduction with LAH; 11 and (vi)

A formal stereoselective synthesis of Herbarumin III has been accomplished starting from butanal involving Maruoka asymmetric allylation, diastereoselective iodine-induced electrophilic cyclization and conversion of iodocarbonate into syn -epoxy alcohol as the key steps.

The synthetic utility of S-mesitylsulfinimines for the synthesis of chiral amines and aziridines was examined through their reactions with Grignard reagents, with the ylides derived from trimethylsulfonium iodide and S-allyl-tetrahydrothiophenium bromide and through an aza-Darzens manifold, affording convenient access to a diverse range of highly substituted chiral amines and aziridines in high yields and excellent stereoselectivities.

N,N′-Diarylureas have been shown to efficiently catalyse sulfonium ylide-mediated aldehyde epoxidation reactions for the first time. These processes are of broad scope and can be coupled with a subsequent Cu(II) ion-catalysed Meinwald rearrangement to give an efficient and convenient protocol for aldehyde homologation without intermediate purification.

N,N′-Diarylureas have been shown to efficiently catalyse sulfonium ylide-mediated aldehyde epoxidation reactions for the first time. These processes are of broad scope and can be coupled with a subsequent Cu(II) ion-catalysed Meinwald rearrangement to give an efficient and convenient protocol for aldehyde homologation without intermediate purification.

The synthetic utility of S-mesitylsulfinimines for the synthesis of chiral amines and aziridines was examined through their reactions with Grignard reagents, with the ylides derived from trimethylsulfonium iodide and S-allyl-tetrahydrothiophenium bromide and through an aza-Darzens manifold, affording convenient access to a diverse range of highly substituted chiral amines and aziridines in high yields and excellent stereoselectivities.

Pyrazolylborate–zinc–thiolate complexes react under mild conditions with methyl iodide, dimethylsulfate and trimethylsulfonium iodide, liberating the corresponding methyl thioethers; the driving force for these reactions lies in the high nucleophilicity of the zinc-bound thiolates and the low donor quality of thioethers toward zinc.

The direct preparation of a range of variously substituted chiral tert-butylsulfinylketimines was achieved in good yield (41–90%), with relatively rapid reaction times (4–15 hours); their synthetic application was examined through the reaction with the ylides derived from trimethylsulfonium iodide and S-allyl tetrahydrothiophenium bromide, affording convenient access to a diverse range of highly substituted chiral aziridines in up to 78% yield and > 90% d.e.

Treatment of chalcones, cyclohexanones and imines with trimethyloxosulfonium or trimethylsulfonium iodide and KOH in the solid state give cyclopropanones, oxiranes and aziridines, respectively, in good yields. Solid-state methylene transfer also occurs enantioselectively when an optically active sulfoximine and/or an optically active host compound is used.

The condensation reaction of trimethylsulfonium iodide with variously functionalized aldehydes and ketones in the presence of solid potassium hydroxide in acetonitrile leads to the selective formation of the corresponding epoxides in high yields. The method used calls upon a solid-liquid transfer process.

1. For the soft rubber stock SB1A, there is no evidence for the change: polysulfide → free sulfur on acetone extraction. 2. Evidence for the change: polysulfide → other sulfur links on acetone extraction is indicated by increased reactivity of extracted SB1A to methyl iodide. 3. Natural and GR-S ebonites lose about one-third of their combined sulfur on reaction with methyl idode at 24° C. Trimethylsulfonium iodide is found in large quantities. 4. Neither extraction experiments nor methyl iodide reactions offer evidence for occurrence of polysulfides in 32 per cent sulfur natural ebonite.

(1976). THE USE OF TRIMETHYLSULFONIUM IODIDE IN THE SYNTHESIS OF BIOLOGICALLY ACTIVE NITROXIDES. Organic Preparations and Procedures International: Vol. 8, No. 4, pp. 159-161.

Reactions of acylacetylenes 1a-h with benzotriazole 2 give intermediates 3a-h. The treatment of 3a-h with trimethylsulfonium iodide in the presence of base give intermediate oxiranes 4a-h and 2,3-benzo-1,3a,6a-triazapentalenes 7d-g depending on substituent. Acid-catalyzed rearrangement of crude 4a-h give 2,4-disubstituted furans 5a-h.