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 language | English (US) |
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Pages (from-to) | 2806-2812 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 40 |
Issue number | 19 |
DOIs | |
State | Published - Sep 1 1975 |
Externally published | Yes |
All Science Journal Classification (ASJC) codes
- Organic Chemistry