Linear free energy relationships in the Bergman cyclization of 4-substituted-1,2-diethynylbenzenes

Nakyen Choy, Chang Sik Kim, Cynthia Ballestero, Leanne Artigas, Christian Diez, Frank Lichtenberger, Jed Shapiro, K. C. Russell

Research output: Contribution to journalArticle

42 Scopus citations

Abstract

A series of 4-substituted-1,2-diethylnylbenzenes were prepared (1a-f) and subjected to Bergman cyclization. Bulk cyclization proceeded to produce the corresponding 2-substituted naphthalenes (2a-f) in good yields (59-78%). Kinetic experiments show a linear free energy relationship between the cyclization rate and the Hammett σ(m) substituent coefficient and the Swain-Lupton field and resonance parameters. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)6955-6958
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number36
DOIs
StatePublished - Sep 2 2000

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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    Choy, N., Kim, C. S., Ballestero, C., Artigas, L., Diez, C., Lichtenberger, F., Shapiro, J., & Russell, K. C. (2000). Linear free energy relationships in the Bergman cyclization of 4-substituted-1,2-diethynylbenzenes. Tetrahedron Letters, 41(36), 6955-6958. https://doi.org/10.1016/S0040-4039(00)01181-3