A COMPARISON OF THE ACID-CATALYZED HYDROLYSIS OF 2-(PHENYLTHIO)TETRAHYDRO-2H-THIOPYRAN IN AQUEOUS PERCHLORIC-ACID WITH THOSE OF ITS O,O-ANALOGS AND O,S-ANALOGS
M. Ali et Dpn. Satchell, A COMPARISON OF THE ACID-CATALYZED HYDROLYSIS OF 2-(PHENYLTHIO)TETRAHYDRO-2H-THIOPYRAN IN AQUEOUS PERCHLORIC-ACID WITH THOSE OF ITS O,O-ANALOGS AND O,S-ANALOGS, Journal of chemical research. Synopses, (11), 1993, pp. 452-453
The relative reactivities of 2-phenoxytetrahydro-2H-pyran (1), 2-(phen
ylthio)tetrahydro-2H-pyran (2) and 2-(phenyl-thio)tetrahydro-2H-thiopy
ran (3) towards acid-catalysed hydrolysis in aqueous perchloric acid a
re 4.2 x 10(5) : 2.4 x 10(2): 1, with 2 (and probably also 1) hydrolis
ing via an Al mechanism, but with 3 showing some shift towards an AS(E
)2 scheme; the results suggest that the hydrolyses of sugars possess s
pecial features.