Indian Journal of Chemistry Vol. 43B, June 2004, pp . 1275-1281 Ceric ammonium nitrate (CAN) catalyzed Baeyer-Villiger oxidation of carbonyl compounds, specially 20-oxosteroids Papori Goswami, Saroj Hazarika, Archana M Das & Pritish Chowdhury* Natural Products Chemistry Division, Regional Research Laboratory, Jorhat 785006, India e-mail:
[email protected] Received 4 February 2003; accepted (revised) 10 December 2003 The role of ceric ammonium nitrate (CAN) as an effective catalyst in the peracid induced Baeyer-Villiger oxidation of carbonyl compounds with special reference to steroids has been demonstrated. IPC: Int.C1.7 C 07 K 1/00 Ceric ammonium nitrate (CAN) finds application in temperature even when kept for more than 48 hr. Fur synthetic organic chemistry for various chemical ther, GLC experiment confirmed 40-55% conversion 2 transformations, viz., nitration 1, nitroacetamidation , of benzophenone 12 to phenyl benzoate 12a in 5 hr complex formation with various alcohols3 etc. Its role when CAN was used as a catalyst along with peracid as single electron oxidant has been reported in a num whereas only 8% conversion was observed in the ab 4 8 ber of publications including some recent reviews - . sence of CAN when kept for more than 24 hr. During CAN-induced oxidative radical transformations of our investigation, we also found that for all the cases 9 steroids have also been reported . We too have re (substrates 5-8, 10, 11, 13-15) the oxidation furni shed ported lO the catalytic action of CAN in the esterifica only one isomer viz. 5a-8a, lOa, lla, 13a-15a as con tion of carboxylic acids in very high yield .