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5709588 
Journal Article 
Aryl vinyl cyclopropane Cope rearrangements 
Allegre, K; Tunge, Jon 
2019 
1 
Tetrahedron
ISSN: 0040-4020 
75 
24 
3319-3329 
English 
WOS:000471208400022 
While the divinyl cyclopropane Cope rearrangement is well-known, and has been broadly applied in synthesis, examples of the aryl vinyl cyclopropane Cope rearrangement are less common and generally limited in scope or reaction yield. The aryl vinyl cyclopropane Cope rearrangement gives access to the benzocycloheptene scaffold, which is present in a variety of naturally occurring and medicinally relevant products. Herein we report a method to obtain either of two regioisomeric benzocycloheptene products via an aryl vinyl cyclopropane Cope rearrangement, featuring additive-controlled regioselectivity. Mechanistic studies indicate a dynamic equilibration of cyclopropane stereoisomers, followed by rearrangement of the cis diastereomer. 
Vinyl cyclopropane; [3,3] sigmatropic rearrangement; Cope rearrangement; Epimerization; Medium ring