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- Ko , S.Y. 1994 . Tetrahedron Lett. , 35 : 3601 A Payne rearrangement of a hydroxymethyl cyclic sulfate, followed by acetylide attack on the resulting epoxide has been reported
- Berridge , M.S. , Franceschini , M.P. , Rosenfield , E. and Tewson , T.J. 1990 . J. Org. Chem. , 55 : 1211 Preparation by the method of Gao and Sharpless[8] is higher yielding and more convenient. Propylene glycol is appreciably hygroscopic, but it may be conveniently dried by azeotropic removal of water with toluene
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- Prepared by bromination of triethyl orthopropionate (Beyerstedt, F.; McElvain, S.M. J. Am. Chem. Soc. 1937, 59, 1273; Walters, P.M.; McElvain, S.M. J. Am. Chem. Soc. 1940, 62, 1482), then elimination, bromination and elimination again (Stetter, H.; Uerdingen, W.; Synthesis 1973, 207; Gassman, P.G.; Chavan, S.P. Tetrahedron Lett. 1988, 29, 3407). For both elimination reactions, powdered KOH in DMSO was used in place of KOt-Bu. An alternative method has been described.[14]
- For the corresponding epoxide reaction, see Boche , G. and Bigalke , J. 1984 . Tetrahedron Lett. , 25 : 955
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- For numerous examples, see Ref.7
- The rapid formation of a cloudy precipitate indicates that sufficient acid has been added. If the mixture is not opaque, hydrolysis of the hemisulfate does not occur and more acid is required