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Synthesis of Z- and E-[2,3-2H2] and [2,3-3H2]-1,1-dichloro-2,3- diphenylcyclopropane (2H- and 3H-analog II and its trans isomer)

✍ Scribed by Billy W. Day; Sastry S. Jonnalagadda

Publisher: John Wiley and Sons
Year: 1995
Tongue: French
Weight: 338 KB
Volume: 36
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580360109

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✦ Synopsis

Abstract

^2^H and ^3^H labeled Z‐ and E‐1,1‐dichloro‐2,3‐diphenylcyclopropane (1 and 2) were synthesized starting from NaB^2^H~4~ and NaB^3^H~4~ reduction of benzil. The resulting glycols were transformed to the 1,2‐labeled Z‐ and E‐stilbenes by thermolysis of their cyclic thionocarbonates in trimethylphosphite. The stilbenes were reacted with phase transfer‐generated dichlorocarbene to form the title compounds. The dideuterio isomers were separated by fractional crystallization in yields of 60 and 48%. Each was greater than 99 % geometrically and 98 % isotopically pure. The ditritio isomers were separated by C‐18 JPLC. The radiochemical yields, on a molar basis using benzil as the limiting reagent, were 42 % and 23 %, each with specific activity of 88.5 mCi/mmol and radiochemical purity of > 95%.

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