Pyridinium chlorochromate in organic synthesis. A facile and selective oxidative cleavage of enol ethers

…, I Islam, M Raghavan, S Chandrasekaran

Index: Baskaran, S.; Islam, I.; Raghavan, Malini; Chandrasekaran, S. Chemistry Letters, 1987 , p. 1175 - 1178

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Citation Number: 15

Abstract

1178 Chemistry Letters, 19 8 7 In this paper we wish to report the realization of such a strategy for effect- ing a smooth oxidative cleavage of nucleophilic olefins such as cyclic enol ethers to keto lactones with pyridinium chlorochromate. In a typical experiment the enol ether (2 mmol in 5 ml of CH-Cl, or benzene) was rapidly added to a suspension of PCC (8 mmol) and Celite (1.5 g) in CH2C12 or benzene (15 ml). After stirring for 1-48 h (25 °C-80 °C), ether (50 ml) ...