Reaction of 1,3-dienes with sulphur dioxide. Part 1. Thermal decomposition of 2,5-dihydrothiophen 1,1-dioxides
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 13,p. 1470-1475
- https://doi.org/10.1039/p29760001470
Abstract
Rates of decomposition of 18 substituted dihydrothiophen 1, 1-dioxides in solution (to yield the corresponding butadiene and SO2) are reported, together with activation parameters and solvent and isotope effects. Rates are mildly accelerated by +M groups at C-3 and by alkyl substituents at C-2 but sterically retarded by bulky groups at C-3 and especially by two β-substituents. 3, 4, 5, 6-Tetrahydro-1H-cyclopenta[c]thiophen 2, 2-dioxide is especially reactive and this is attributed to strain release during fragmentation. The reactions accord in general with requirements for a chelotropic reaction.Keywords
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