20849-33-6Relevant articles and documents
Kinetics and mechanism of the aminolysis of phenyl dithiobenzoates
Oh, Hyuck Keun,Shin, Chul Ho,Lee, Ikchoon
, p. 1169 - 1174 (2007/10/02)
The kinetics and mechanism of the reactions of phenyl dithiobenzoates with anilines in acetonitrile at 55.0 deg C have been studied.The large magnitude of βx(βnuc) and the signs of cross-interaction constants, ρeXY > 0, ρYZ XZ > 0, are all consistent with the carbonyl addition mechanism in which the breakdown of the tetrahedral intermediate, T+/-, is rate limiting.The thiocarbonyl group (C=S) is found to favour amine expulsion in contrast to the carbonyl group (C=O) which favours the S-bonded nucleofuge expulsion from T+/-.The signs of cross-interaction constants, ρXY, ρYZ and/or ρXZ, are shown to provide useful mechanistic criteria for distinguishing, especially, the carbonyl addition mechanism involving the rate-limiting breakdown of the tetrahedral intermediate (T+/- from the concerted SN2 mechanism.
BENZYNE-INDUCED FRAGMENTATION REACTIONS OF 1,3-DITHIOLANES
Nakayama, Juzo,Ozasa, Hiroshi,Hoshino, Masamatsu
, p. 1053 - 1056 (2007/10/02)
2-Monosubstituted 1,3-dithiolanes, on reaction with benzyne, undergo two types of fragmentation, one of which gives phenyl vinyl sulfide and thioaldehydes (corresponding aldehydes as the final products) and the other gives phenyl dithiocarboxylates and et
