Stereodirecting effects in the characterization of ylide intermediates in reactions of singlet methylene with an allylic ether and an allylic chloride
Document Type
Article
Department or Administrative Unit
Chemistry
Publication Date
7-1997
Abstract
The stereodirecting effects of substrate substituents were examined in addition of 1:CH2 to the double bonds of 3-methoxycyclohexene (3a), 3-chlorocyclohexene (3b), and 3-methylcyclohexene (3c) in pentane solution at temperatures from 23°C to −50°C. A preference for addition syn to the directing substituent was observed in reactions of 3a and 3b and was attributed to a reversible interaction of carbene and substituent. In the reaction with 3a this interaction was not obviously ylide formation.
Recommended Citation
Cubbage, J. W., Edelbach, B. L., Kuen, K. S., & DeLuca, J. A. P. (1997). Stereodirecting Effects in the Characterization of Ylide Intermediates in Reactions of Singlet Methylene with an Allylic Ether and an Allylic Chloride. Tetrahedron, 53(29), 9823–9834. https://doi.org/10.1016/s0040-4020(97)00329-3
Journal
Tetrahedron
Rights
© 1997 Elsevier Science Ltd.
Comments
This article was originally published in Tetrahedron. The full-text article from the publisher can be found here.
Due to copyright restrictions, this article is not available for free download from ScholarWorks @ CWU.