Antibacterial benzisoxazolones. An unusual rearrangement product from o-nitrostyrene oxide en route to the photolabile carbonyl protecting group,(o-nitrophenyl) …

W Wierenga, AW Harrison, BR Evans…

Index: Wierenga, Wendell; Harrison, Allen W.; Evans, Bruce R.; Chidester, Connie G. Journal of Organic Chemistry, 1984 , vol. 49, # 3 p. 438 - 442

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Citation Number: 22

Abstract

In the process of synthesizing the known, photolabile protecting group (0-nitropheny1) ethylene glycol, we uncovered an acid-mediated rearrangement of o-nitrostyrene oxide to l- (hydroxymethyl)-2, l-benzisoxazo1-3 (~-one. The structure was ascertained by IR, UV,'H NMR, 13C NMR, MS, and X-ray crystallography. Also the benzisoxazolone was prepared by independent synthesis from an o-nitrobenzoate. Another novel transformation uncovered ...