DOI: 10.1055/s-0036-1588451
© Georg Thieme Verlag Stuttgart · New York

Reactivity of Seven-Membered-Ring trans-Alkenes with Electrophiles

Jillian R. Sanzone, K. A. Woerpel*
  • Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003, USA   Email:
This research was supported by the National Science Foundation (CHE-1362709). J.R.S. was supported by a Margaret Strauss Kramer Fellowship from the NYU Department of Chemistry
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Publication History

Received: 10 April 2017

Accepted after revision: 10 May 2017

Publication Date:
21 June 2017 (eFirst)

Published as part of the Cluster Silicon in Synthesis and Catalysis


Seven-membered-ring trans-alkenes containing a silicon–oxygen bond reacted rapidly with oxygen gas and electron-deficient alkenes and alkynes to give products with high selectivity. Addition of an electron-donating substituent or incorporating additional strain increased the reactivity by over two orders of magnitude. These results indicate that release of strain is not the only driving force for reactivity.

Supporting Information