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Photo-Fries Rearrangements of 1-naphthyl (R)-2-phenylpropanoate in Poly(vinyl Acetate) and Ethyl Acetate. Influence of Medium Polarity and Polymer Relaxation on Motions of Singlet Radical Pairs

Photo-Fries Rearrangements of 1-naphthyl (R)-2-phenylpropanoate in Poly(vinyl Acetate) and Ethyl Acetate. Influence of Medium Polarity and Polymer Relaxation on Motions of Singlet Radical Pairs

Jinqi Xu, Mathew George, Richard G Weiss

An Acad Bras Cienc. 2006 Mar;78(1):31-44.

PMID: 16532205

Abstract:

Both the regio- and stereo-chemistries of the photoreactions of 1-naphthyl (R)-2-phenylpropanoate have been investigated in poly(vinyl acetate) films in their glassy (at 5 degrees C) and melted (at 50 degrees C) states and in ethyl acetate. These results are compared with those from irradiations in polyethylene films and in n-hexane. The regioselectivity of the intermediate 1-naphthoxy/(R)-2-phenylpropanoyl radical pair combinations is much higher in both the melt and glassy states of poly(vinyl acetate) films than that in the melt state of completely amorphous polyethylene films, but the stereoselectivity of intermediate prochiral 1-naphthoxy/1-phenylethyl radical pair combinations is much lower in poly(vinyl acetate). The results emphasize the need to control the ratio between the rates of radical tumbling and translation, as well as the ratio between the rates of in-cage motions and cage-escape, if high stereo- and regio-selectivities of combination products are to be achieved. A mechanistic picture of how the radicals of the intermediate pairs are affected by and interact with the various media is advanced.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS775180	Poly[N-(1-naphthyl)-N-phenylmethacrylamide]			Price

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