Conformational analysis. Part VII. 2-Alkyl-4-methyl- and 2-alkyl-2,4-dimethyl-1,3-dithiolans
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 10,p. 1376-1379
- https://doi.org/10.1039/p29730001376
Abstract
2-Alkyl-4-methyl- and 2-alkyl-2,4-dimethyl-1,3-dithiolans have been prepared and studied by means of the acid-cataysed equilibration of the diastereoisomers and 1H n.m.r. spectroscopy. Free energy differences between diastereoisomers are small and within the range 0·13–0·54 kJ mol–1 for the dialkyl series and 0·71–1·00 kJ mol–1 for the trialkyl series. The data suggest that the dithiolan ring is quite a flexible system and a possible minium energy conformation can be defined only if there is a bulky substituent at the 2-position.Keywords
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