Thermal isomerization of cis,anti,cis-tricyclo[6.3.0.0(2,7)]undec-3-ene to endo-tricyclo[5.2.2.0(2,6)]undec-8-ene

John E Baldwin; Andrew R Bogdan; Phyllis A Leber; David C Powers

doi:10.1021/ol052004k

Thermal isomerization of cis,anti,cis-tricyclo[6.3.0.0(2,7)]undec-3-ene to endo-tricyclo[5.2.2.0(2,6)]undec-8-ene

Org Lett. 2005 Nov 10;7(23):5195-7. doi: 10.1021/ol052004k.

Authors

John E Baldwin¹, Andrew R Bogdan, Phyllis A Leber, David C Powers

Affiliation

¹ Department of Chemistry, Syracuse University, Syracuse, New York 13244, USA.

PMID: 16268536
DOI: 10.1021/ol052004k

Abstract

[reaction: see text] The gas-phase thermal isomerization of cis,anti,cis-tricyclo[6.3.0.0(2,7)]undec-3-ene (1) to endo-tricyclo[5.2.2.0(2,6)]undec-8-ene (2) at 315 degrees C occurs cleanly through a symmetry-forbidden [1,3] suprafacial,retention (sr) pathway.