Experimental tests of the stereoelectkoic effect at phosphoru: Michaelis-Arbusov reactivity of phosphite esters |
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Authors: | Kazunari Taira David C Gorenstein |
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Institution: | Chemistry Department, University of Illinois at Chicago, Box 4348 Chicago, IL 60680 U.S.A. |
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Abstract: | Whereas triethyl phosphite readily reacts with benzoyl chloride to yield the Michaelis-Arbusov product, diethyl benzoyl phosphonate, 1-methyl-4-phospha-3,5,8-trioxabi)cyclo2.2.2]octane, , is essentially unreactive, even at a higher temperature. The bicyclic phosphite also reacts slower than the triethyl phosphite In an oxidation with t-butyl hydroperoxide. These results are interpreted in terms of the stereoelectronic effect. |
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