The Sommelet Type Rearrangement of Certain Trithioorthoesters

References

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• The intramolecular substitution by the anionic end of 2 is accompanied by bond cleavage between C-2 and the anionic methylenethio group, while the bond between C-2 and S-3 of the 1,3-dithiane ring is not broken. The justification of this mechanism lies basically in the intuitive feeling that the endocyclic C-S bond is more stable than the exocyclic one. If the bond cleavage between the C-2 and S-3 occurred in the reaction, the final products would be 1-alkylthio-3-[(1-alkyl-2-thiaindan-1-yl)thio]propanes. However, the observation on the 1H-NMR and 13C-NMR spectral data leads to the prediction that the obtained products are 6 and not the compounds having 2-thiaindan moiety
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