Abstract
Abstract Oxidation of 1,8-bis(allylthio)naphthalene (1) with mCPBA gave the monooxide (2) which underwent three consecutive sigmatropic rearrangements, namely the Mislow-Evans, [2.3] S-S and the thio-Claisen rearrangements to afford 2-allyl-naphtho[1,8-cd]-1,2-dithiole (4) and prop-2-enol (5) quantitatively. In the sulfoxide (2) and sulfenate (3), the second allylsulfenyl sulfur atom may attack transannularly the sulfinyl or sulfenate sulfur atom to promote the rearrangement, since the rate of this thio-Claisen rearrangement of 2 was rapid as compared with that of the normal thio-Claisen rearrangement of allyl phenyl sulfide which requires a temperature of more than 200 °C.
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