The Formation of an Enantiomerically Pure Product of Free Radical Coupling. The Chemistry of Diphenylcarbene in Polycrystalline (S)-(+)-2-Butanol
Photolysis of 0.1 M diphenyldiazomethane at 77 K or 137 K in solid (S)-(+)-2-butanol gives tertiary alcohol 9 along with other products.Compound 9 was isolated and found to be enantiomerically pure by chiral NMR shift reagents.Compound 9 is formed by reaction of triplet diphenylcarbene with (S)-(+)-2-butanol to give a radical pair which subsequently collapses.The solid-state matrix directs the radical pair collapse with complete retention of configuration.
Zayas, Jose,Platz, Matthew S.
p. 7065 - 7069
(2007/10/02)
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