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Synthesis of Z ‐ and E ‐[2,3‐ 2 H 2 ] and [2,3‐ 3 H 2 ]‐1,1‐dichloro‐2,3‐ diphenylcyclopropane ( 2 H‐ and 3 H‐analog II and its trans isomer)
Author(s) -
Day Billy W.,
Jonnalagadda Sastry S.
Publication year - 1995
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580360109
Subject(s) - chemistry , benzil , dichlorocarbene , reagent , limiting , nuclear chemistry , medicinal chemistry , organic chemistry , catalysis , mechanical engineering , engineering
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%.