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Kinetic isotope effects on metaphosphate generation from fragmentation of 2,3-oxaphosphabicyclo[2.2.2]octene derivatives

✍ Scribed by Stefan Jankowski; Juliusz Rudziński

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 556 KB
Volume: 7
Category: Article
ISSN: 1042-7163
DOI: 10.1002/(sici)1098-1071(199610)7:5<369::aid-hc14>3.0.co;2-o

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✦ Synopsis

Kinetic isotope effects of deuterium and oxygen-1 8 were measured on fragmentation of syn-3-ethoxy (la)

The secondary deuterium isotope effect on hydrogen adjacent to the P-C bond was found to be 1.060 & 0.008 for la and 1.081 f 0.009 for lb. The kinetic oxygen isotope effect on the bridge P-0-C is 0.9901 k 0.0016 for la. The data indicate an unsymmetrical transition state for retrocycloaddition extrusion of the metaphosphate moiety, with the breakage of the C-P bond and formation of the P = 0 bond more advanced than the C-0 breakage. A synthesis of l a and 1 b labeled with deuterium is described.

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