Abstract
Abstract 9,9-Bis(ethylthio)fluorene (1a) reacted with sodium ethanethiolate in methanol to give 9-ethylthiofluorene and diethyl disulfide suggesting that a C–S bond cleavage occurs by attack of a nucleophile at sulfur if a leaving group is sufficiently stable. The pseudo-first-order rate constans for the reaction of 1a and methoxycarbonyl-substituted 9-ethylthiofluorenes have suggested that the methoxycarbonyl group at 1-position exerts through space interaction with sulfur atom(s). The rate constants for ester exchange in 1-methoxycarbonylfluorene and its derivatives have been discussed on the ground of neighboring sulfur participation.
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