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Synthesis of 13C and 2H-labelled 2-phenylcyclododecanones

✍ Scribed by V. Pushkara Rao; Jin-Feng Wang; Nicholas J. Turro; Charles Doubleday Jr.

Publisher
John Wiley and Sons
Year
1990
Tongue
French
Weight
415 KB
Volume
28
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

^13^C labelled (1,2 and 1,12) and perdeuterated derivatives of 2‐phenyl cyclododecanones, as precursors for labelled triplet flexible biradicals to probe magnetic isotope effects at the radical centers on the triplet decay dynamics, were synthesized. Isotopomers of 2‐phenylcyclododecanone‐^13^C~2~‐(1,2 and 1,12) were synthesized from cyclododecanone‐^13^C~2~‐(1,2) by dibromination, followed by phenylation with lithiumdiphenylcuprate. Cyclododecanone‐^13^C~2~‐(1,2) was obtained from 1, 10‐dibromodecane via the following sequence: (1) K^13^CN; (2) hydrolysis; (3) esterification; (4) acyloin condensation. Perdeuterio‐2‐phenyl cyclododecanone (95% isotopic purity) was prepared from unlabelled 2‐phenyl cyclododecanone by a substitution of deuterium for hydrogen by treatment with excess D~2~O, catalyzed with D~2~‐reduced PtO~2~ in the presence of D~2~O~2~.

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