Tert-butyldiphenylsilylmethyl triflate: Preparation and dipolar cycloaddition reactions of 1-(tert-butyldiphenylsilylmethyl)-6-cyano-4-methyl-1,2,5,6-tetrah ydropyridine

Article abstract of DOI:10.1080/00397910008086931

Alkylation of substituted pyridines with tert-butyldiphenylsilylmethyl triflate provides N-[tert-butyldiphenylsilylmethyl]pyridinium triflates in excellent yields. Reductive cyanation of the pyridinium triflates provides 1-(tert-butyldiphenylsilylmethyl)-6-cyano-1,2,5,6-tetrahydropyrid ines, azomethine ylid precursors, in modest yields. An unexpected dipolar cycloaddition reaction of an ylid derived from the title 6-cyanopiperidine is described.

Full text of DOI:10.1080/00397910008086931

Synthetic Communications
ISSN: 0039-7911 (Print) 1532-2432 (Online) Journal homepage: http://www.tandfonline.com/loi/lsyc20
Tert-Butyldiphenylsilylmethyl Triflate: Preparation
and Dipolar Cycloaddition Reactions of 1-
(Tert-Butyldiphenylsilylmethyl)-6-Cyano-4-
Methyl-1,2,5,6-Tetrahydropyridine
David J. Hart & Ying Huan
To cite this article: David J. Hart & Ying Huan (2000) Tert-Butyldiphenylsilylmethyl Triflate:
Preparation and Dipolar Cycloaddition Reactions of 1-(Tert-Butyldiphenylsilylmethyl)-6-
Cyano-4-Methyl-1,2,5,6-Tetrahydropyridine, Synthetic Communications, 30:17, 3203-3213, DOI:
10.1080/00397910008086931
To link to this article: http://dx.doi.org/10.1080/00397910008086931
Published online: 04 Dec 2007.
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Date: 27 October 2015, At: 14:24