Synthesis and Solvolysis of Tricyclo[4.3.2.02,5]undeca-3,8,10-trien-7-ol. An Unusual [CH]11+ Rearrangement

John T. Groves, Christian A. Bernhardt

Research output: Contribution to journalArticle

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Abstract

Synthesis of the title compound (11) has been achieved by two routes, the cycloaddition of cyclobutadiene to tropone and addition of tetrachlorocyclopropene to an appropriate bicyclo[4.2.0]diene (6) and subsequent transformations. Acetolysis of esters of 11 afforded a rearranged allylic acetate (15) and dihydroindenylenol acetate (20). Deuterium-labeling studies indicate that 20 derives from 15 via a bicyclo[2.1.0]pentane (25) and subsequent thermal fission. Activation parameters for this process (ΔH = 31.2 kcal/m ΔS = -6.2 eu) are in accord with the proposed mechanism.

Original languageEnglish (US)
Pages (from-to)2806-2812
Number of pages7
JournalJournal of Organic Chemistry
Volume40
Issue number19
DOIs
StatePublished - Sep 1 1975
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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