The Chemistry of Short-Lived α-Fluorocarbocations

1Citations
Citations of this article
13Readers
Mendeley users who have this article in their library.

This article is free to access.

Abstract

The present study of the chemistry of short-lived α-fluorocarbocations reveals that even inactive methyl carbons can serve as nucleophiles, attacking a cationic center. This, in turn, facilitates the synthesis of a cyclopropane ring in certain triterpene backbones. We report the synthesis of compounds similar to 2, containing a bridgehead cyclopropane, and compounds of type 3 with an 11 membered bicyclic ring consisting of two bridgehead double bonds (anti-Bredt) within a triterpene skeleton. The synthesis involves three unconventional chemical processes: (a) a methyl group serving as a nucleophile; (b) the unexpected and unprecedented synthesis of a strained system in the absence of an external neighboring trigger; and (c) the formation of an 11-membered bicyclic diene ring within a triterpenoid skeleton. An α-fluorocarbocation mechanism is proposed and supported by density functional theory calculations.

Cite

CITATION STYLE

APA

Rozen, S., Vints, I., Lerner, A., Hod, O., Brothers, E. N., & Moncho, S. (2021). The Chemistry of Short-Lived α-Fluorocarbocations. Journal of Organic Chemistry, 86(5), 3882–3889. https://doi.org/10.1021/acs.joc.0c02731

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free