The steric course of the formation of benzocyclobutene by thermal desulphonylation of 1,3-dihydrobenzo[c]thiophen 2,2-dioxide
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 9,p. 541-542
- https://doi.org/10.1039/c39720000541
Abstract
Thermolysis of cis-[1,3-2H2]-dihydrobenzo[c]thiophen 2,2-dioxide (1b) gives trans-[1,2-2H2]-benzocyclobutene (3b); in conjunction with the Woodward–Hoffmann rules and the stereochemistry of closely related reactions, this provides strong evidence for a mechanism involving disrotatory formation of o-quinodimethane (2) with extrusion of sulphur dioxide, followed by conrotatory closure of (2) to benzocyclobutene.Keywords
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