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The reaction of pentasubstituted 3-hydroxy-1,2-dioxolanes (hemiperketals) with trivalent phosphorus compounds: Synthesis of β-hydroxy ketones

✍ Scribed by Alfons L. Baumstark; Pedro C. Vasquez; Yaxiong Chen

Publisher: John Wiley and Sons
Year: 1993
Tongue: English
Weight: 400 KB
Volume: 4
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.520040209

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✦ Synopsis

The reaction of a series of 4,4-dimethyl-3,5,5-(R3, R2,

RI)-3-hydroxy-I,2-dioxolanes la-d [la (R,

with trimethyl phosphite or triphenylphosphine produced the p-hydro.xy ketones, 2a-d [(R,R#70H)CMe2-COR3], and the corresponding phosphoryl compounds in high yield. The reactions were slow (-24 hours), requiring excess of the trivalent phosphorus compounds for optimum results. The reaction was found to be of the second order overall, first order in peroxide and in phosphoms reagent. Triphenylphosphine was found to be more reactive than trimethyl phosphite. Formal substitution of a phenyl group for

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