Intramolecular participation in hypervalent iodine oxidation. The synthesis of coumaran-3-ones, aurone, and isoaurone

…, O Prakash, I Prakash, HA Musallam

Index: Moriarty, Robert M.; Prakash, Om; Prakash, Indra; Musallam, H. A. Journal of the Chemical Society, Chemical Communications, 1984 , # 20 p. 1342 - 1343

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Citation Number: 19

Abstract

Oxidation of various acetophenone derivatives with PhI- ( OAc)2/KOH-MeOH yields the corresponding a-hydroxy- dimethyl acetal.1 In this transformation -0Me plays the role of an external nucleophile. We now show that an o-hydroxy group in various substi- ... 0 'OMe /I 'OMc (A) - -C-CH2 ... (1) (2) (2a) R3 = OMe (tb) R3 = Me (23 R3 = OMe ... (la) R1 = R2 = R3 = H (lb) R1 = R2 = H; R3 =Me (lc) R1 = R2 = Me; R3= H (Id) R' = R2 = H; R3 = CHzPh (2d) R3 = CH2Ph

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