123630-35-3Relevant academic research and scientific papers
Divergent Thermal Behaviour of Phenoxymethyl Phenyl Sulphoxide under Gas- and Condensed-phase Conditions
Banks, Malcolm R.,Brown, Angus R.,Cameron, Donald K.,Gosney, Ian,Cadogan, J. I. G.
, p. 595 - 598 (2007/10/02)
A comparison is made between the behaviour of phenoxymethyl phenyl sulphoxide (2) under different thermolytic conditions.Passage of (2) through a quartz tube in the gas phase at 600 deg C results in products which can be rationalised by assuming homolytic cleavage of the S-C bond and the generation of both the phenylsulphinyl (4) and phenoxymethyl (6) radicals which decompose by separate pathways to yield S-phenyl benzenethiosulphonate (3) and benzaldehyde, respectively.On the other hand, solution thermolysis of (2) in 2H8>toluene at 110 deg C leads to a facile S->O 1,2-shift abd the formation of thermally stable phenoxymethyl benzenesulphonate (9) in quantitative yield.A bimolecular oxygen-transfer mechanism is proposed for the conversion of (2) into (9) which is rationalised in terms of a double (stabilising) anomeric effect brought about by the acetal group in (9).Cross-over experiments support the mechanism.
