Mitsunobu Nakamura, Yasuhiro Osako, Y. Okamoto
Dec 1, 1993
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Influential Citations
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Journal
Phosphorus Sulfur and Silicon and The Related Elements
Abstract
Abstract Photosubstitution of diethyl methoxyphenyl phosphate with some nucleophiles (Cl−, Br−, CN−) in methanol gave the corresponding 4-chloro-, 4-bromo-, and 4-cyanomethoxybenzenes through a singlet excited state. In acidic media, the reaction was accelerated. Upon further irradiation, halo-substituted methoxybenene underwent dehalogenation to give methoxybenzene. Methoxybenzene also formed directly through the homolytic PO-Ar bond cleavage. The order of reactivities of the isomers of the phosphate was 4->2->3-methoxyphenyl derivatives.