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Rearrangement reactions of 1,1-divinyl-2-phenylcyclopropanes

Hay, EB and Zhang, H and Curran, DP (2015) Rearrangement reactions of 1,1-divinyl-2-phenylcyclopropanes. Journal of the American Chemical Society, 137 (1). 322 - 327. ISSN 0002-7863

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Abstract

1,1-Divinyl-2-phenylcyclopropanes are entry points to a rich area of rearrangement chemistry. With N,N-diallyl amide substrates, tandem radical cyclizations can be initiated at room temperature. Warming provides products of pure thermal rearrangements with acids, ester, and amides. These isomerizations give vinylcyclopentenes resulting from divinylcyclopropane rearrangements and more deeply rearranged tricyclic spirolactams resulting from aromatic Cope rearrangements followed by ene reactions. Conversion of the carbonyl group to an alcohol or ether opens retro-ene pathways followed by either tautomerization or Claisen rearrangement.

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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Hay, EB
Zhang, H
Curran, DPcurran@pitt.eduCURRAN
Date: 14 January 2015
Date Type: Publication
Journal or Publication Title: Journal of the American Chemical Society
Volume: 137
Number: 1
Page Range: 322 - 327
DOI or Unique Handle: 10.1021/ja510608u
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0002-7863
Other ID: NLM PMC4304479 [Available on 12/05/15]
PubMed Central ID: PMC4304479
PubMed ID: 25530073
Date Deposited: 17 Jul 2015 20:06
Last Modified: 30 Mar 2021 12:56
URI: http://d-scholarship.pitt.edu/id/eprint/25653

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