Photochemical reactivity of keto imino ethers. VI. Type I rearrangement and (2+ 2) photocycloaddition to the carbon-nitrogen double bond of 2-oxazolin-4-ones

RM Rodehorst, TH Koch

Index: Rodehorst,R.M.; Koch,T.H. Journal of the American Chemical Society, 1975 , vol. 97, p. 7298 - 7304

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Citation Number: 25

Abstract

Abstract: The Norrish type I cleavage and (2+ 2) photocycloaddition reactions of five oxazolinones, 2-phenyl-(7a), 2-ethoxy-(7b), 2-p-methoxyphenyl-(7~). 2-m-methoxyphenyl- (la), and 2-(rn-trifluoromethylphenyl)-2-oxazolin-4-one(le), are described. The Norrish type I cleavage yields oxiryl isocyanates loa, lob, and lOe, and the (2+ 2) photocycloaddition of the oxazolinones to 1, l-dimethoxyethene and furan yields the azabicyclic products lla, llc, lld, ...