- REACTION OF CHLOROSULFONYL ISOCYANATE WITH 1,2-DIOLS: REARRANGEMENT AND FORMATION OF CARBONATES
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1,2-Diols, 1a-e, upon reaction with chlorosulfonyl isocyanate (CSI) gave the ketones, 3a-e.Under similar experimental conditions, 1,2-diols, 1f-k, gave carbonyl compounds, 3f-k, carbonates, 6f-k, carboxamides, 7h,i, and the epoxide, 5i.
- Joseph, Sajan P.,Dhar, D. N.
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p. 2295 - 2302
(2007/10/02)
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- Formation of Cyclic Carbonates in the Reaction of 1,2-Ditertiary Diols with Acetic Anhydride and 4-(Dimethylamino)pyridine
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The reaction of 1,2-ditertiary diol 1a with acetic anhydride and 4-(dimethylamino)pyridine (DMAP) at high concentrations in the absence of solvent has been found to give rise to cyclic carbonate 2a.The reaction has been generalized with a few other 1,2-ditertiary diols (1b-d).Based on the different products isolated in these reactions, apart from a small amount of normal acetylation products, various mechanisms have been proposed and examined.Tertiary alcohols have been found to give monoacetoacetates in addition to the acetates, under the same conditions.Detailedinvestigations have prompted us to suggest the intermediacy of ketene and diketene in these reactions.
- Bhushan, Vidya,Chakraborty, Thushar K.,Chandrasekaran, Srinivasan
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p. 3974 - 3978
(2007/10/02)
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