Stereodirecting effects in the characterization of ylide intermediates in reactions of singlet methylene with an allylic ether and an allylic chloride

Authors

Jerry W. Cubbage, Illinois State University
Brian L. Edelbach, Illinois State University
Kan Shuh Kuen, Illinois State University
JoAnn P. DeLuca, Central Washington University

Department or Administrative Unit

Chemistry

Document Type

Article

Author Copyright

© 1997 Elsevier Science Ltd.

Publication Date

7-1997

Journal

Tetrahedron

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.

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.

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