Structure dependent rearrangement of the cyclopropylmethyl cation - isolation of a bicyclo[3.2.0]heptene

Nadany, A.E. and McKendrick, J.E. ORCID: https://orcid.org/0000-0003-2275-0569 (2007) Structure dependent rearrangement of the cyclopropylmethyl cation - isolation of a bicyclo[3.2.0]heptene. Tetrahedron Letters, 48 (23). pp. 4071-4074. ISSN 0040-4039 doi: 10.1016/j.tetlet.2007.04.009

Abstract/Summary

Access to 7-allyl substituted norbornene derivatives for tandem olefin metathesis via cationic rearrangement of cyclopropylmethanol substituted norbornenes is shown to be structure dependent. In some cases products that arise from cationic rearrangement of a cyclopropylmethyl cation are furnished. Thionyl chloride is shown to be superior to silica for inducing the desired rearrangement. (c) 2007 Elsevier Ltd. All rights reserved.