The carbene fragmentation-ring expansion route to bridgehead carbocations

Robert A Moss; Fengmei Zheng; Jean-Marie Fedé; Ronald R Sauers

doi:10.1021/ol020083j

The carbene fragmentation-ring expansion route to bridgehead carbocations

Org Lett. 2002 Jul 11;4(14):2341-4. doi: 10.1021/ol020083j.

Authors

Robert A Moss¹, Fengmei Zheng, Jean-Marie Fedé, Ronald R Sauers

Affiliation

¹ Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, New Brunswick, New Jersey 08903, USA. moss@rutchem.rutgers.edu

PMID: 12098242
DOI: 10.1021/ol020083j

Abstract

[reaction: see text]The products, kinetics, and activation parameters were determined for the fragmentation-ring expansions of 1-norbornylmethyloxychlorocarbene (11) and 3-noradamantylmethyloxychlorocarbene (17). Products from 11 (in dichloroethane) included 1-chlorobicyclo[2.2.2]octane (9, 56%) and 1-chlorobicyclo[3.2.1]octane (10, 37%); from 17, we obtained 1-chloroadamantane (15, 68%) and protoadamantyl chloride (16, 28%).