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

N. Choy, C. S. Kim, C. Ballestero, L. Artigas, Christian Diez, F. Lichtenberger, J. Shapiro, K. C. Russell

Research output: Contribution to journalArticle

41 Citations (Scopus)

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

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Cyclization
Free energy
Naphthalenes
Kinetics
Experiments

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Choy, N., Kim, C. S., Ballestero, C., Artigas, L., Diez, C., Lichtenberger, F., ... Russell, K. C. (2000). Linear free energy relationships in the Bergman cyclization of 4-substituted-1,2-diethynylbenzenes. Tetrahedron Letters, 41(36), 6955-6958.

Linear free energy relationships in the Bergman cyclization of 4-substituted-1,2-diethynylbenzenes. / Choy, N.; Kim, C. S.; Ballestero, C.; Artigas, L.; Diez, Christian; Lichtenberger, F.; Shapiro, J.; Russell, K. C.

In: Tetrahedron Letters, Vol. 41, No. 36, 02.09.2000, p. 6955-6958.

Research output: Contribution to journalArticle

Choy, N, Kim, CS, Ballestero, C, Artigas, L, Diez, C, Lichtenberger, F, Shapiro, J & Russell, KC 2000, 'Linear free energy relationships in the Bergman cyclization of 4-substituted-1,2-diethynylbenzenes', Tetrahedron Letters, vol. 41, no. 36, pp. 6955-6958.
Choy N, Kim CS, Ballestero C, Artigas L, Diez C, Lichtenberger F et al. Linear free energy relationships in the Bergman cyclization of 4-substituted-1,2-diethynylbenzenes. Tetrahedron Letters. 2000 Sep 2;41(36):6955-6958.
Choy, N. ; Kim, C. S. ; Ballestero, C. ; Artigas, L. ; Diez, Christian ; Lichtenberger, F. ; Shapiro, J. ; Russell, K. C. / Linear free energy relationships in the Bergman cyclization of 4-substituted-1,2-diethynylbenzenes. In: Tetrahedron Letters. 2000 ; Vol. 41, No. 36. pp. 6955-6958.
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