Investigation on the regioselectivities of intramolecular oxidation of unactivated CH bonds by dioxiranes generated in situ

…, L He, XC Wang, Z Yan, YC Tang, D Yang

Index: Wong, Man-Kin; Chung, Nga-Wai; He, Lan; Wang, Xue-Chao; Yan, Zheng; Tang, Yeung-Chiu; Yang, Dan Journal of Organic Chemistry, 2003 , vol. 68, # 16 p. 6321 - 6328

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Citation Number: 32

Abstract

We found that dioxiranes generated in situ from ketones 1-6 and Oxone underwent intramolecular oxidation of unactivated CH bonds at δ sites of ketones to yield tetrahydropyrans. From the trans/cis ratio of oxidation products 1a and 2a as well as the retention of the configuration at the δ site of ketone 5, we proposed that the oxidation reaction proceeds through a concerted pathway under a spiro transition state. The ...