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Your search keyword '"2,3-sigmatropic rearrangement"' showing total 2 results
Start Over Descriptor "2,3-sigmatropic rearrangement" Database Academic Search Index
2 results on '"2,3-sigmatropic rearrangement"'

1. Preparation of (Z)-1-fluoro-1-alkenyl carboxylates, carbonates and carbamates through chromium mediated transformation of dibromofluoromethylcarbinyl esters and the reactivity as double acyl group donors

Author

Saito, Akio, Tojo, Manabu, Yanai, Hikaru, Wada, Fukiko, Nakagawa, Muga, Okada, Midori, Sato, Azusa, Okatani, Rieko, and Taguchi, Takeo

Subjects
*ALKENYL group, *CARBONATES, *CARBAMATES, *CARBOXYLATES, *CHROMIUM, *ESTERS, *ACYL group
Abstract

Abstract: CrCl2/Mn-mediated transformation of various dibromofluoromethylcarbinyl esters including carboxylates, carbonates and carbamates provided 1-fluoro-1-alkenyl esters via [2,3]-sigmatropic rearrangement of ester group. Reaction proceeded by using CrCl2/Mn system under mild conditions (in THF at room temperature) to give 1-fluoro-1-alkenyl esters in good yield with an excellent Z selective manner. 1-Fluoro-1-alkenyl ester thus obtained acts as a double acyl donor in the reaction with necleophiles such as amine, thiol, alcohol as well as bifunctional necleophiles such as ethylene diamine derivative. [Copyright &y& Elsevier]

Published
2012
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2. Further studies on vinamidinium salt amine exchange reactions, borohydride reductions, and subsequent transformations

Author

Gupton, John T., Telang, Nakul, Jia, Xin, Giglio, Benjamin C., Eaton, James E., Barelli, Peter J., Hovaizi, Mona, Hall, Kayleigh E., Welden, R. Scott, Keough, Matthew J., Worrall, Eric F., Finzel, Kara L., Kluball, Emily J., Kanters, Rene P.F., Smith, Timothy M., Smith, Stanton Q., Nunes, Shane R., Wright, Mathew T., and Birnstihl, Jennifer M.

Subjects
*AMIDINES, *SALT, *AMINES, *SODIUM borohydride, *EXCHANGE reactions, *PHASE transitions, *ALKYLATION, *REARRANGEMENTS (Chemistry)
Abstract

Abstract: Studies directed at the amine exchange reaction of vinamidinium salts followed by sodium borohydride reduction to secondary and tertiary allylic amines are described. The tertiary allylic amines were alkylated and subjected to base mediated rearrangement to yield a variety of highly functionalized tertiary homoallylic amines. [ABSTRACT FROM AUTHOR]

Published
2010
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