84966-04-1Relevant articles and documents
THE EFFECTS OF THE NEIGHBORING METHOXYCARBONYL GROUP AND SULFUR ATOM(S) IN THE CARBON-SULFUR BOND CLEAVAGE AND THE ESTER EXCHANGE IN FLUORENE SYSTEMS
Nakanishi, Waro,Nakanishi, Hitoshi,Yanagawa, Yuko,Ikeda, Yoshitsugu,Oki, Michinori
, p. 105 - 108 (2007/10/02)
9,9-bis(ethylthio)fluorene (1a) reacted with sodium ethanethiolate in methanol ro 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 eith sulfur atoms(s).The rate constants for ester exchange in 1-methoxycarbonylfluorene and its derivatives have been discussed on the ground of neighboring sulfur participation.