Preparation, NMR characterization, and labeling reactions of tritiated borane-THF complex and high specific radioactivity

Journal Article · Fri Nov 17 04:00:00 EST 1995 · Journal of Organic Chemistry

OSTI ID:182235

Chit, Than; Hiromi, Morimoto; Andres, H ^[1]

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1. Lawrence Berkeley National Lab., CA (United States); and others

Borane-tetrahydrofuran complex is a selective, electrophilic reducing agent. The authors report a simple and facile synthesis of tritiated borane-THF complex at high specific radioactivity. Li-{sup 3}H, synthesized from carrier-free tritium gas and dispersed in dry tetrahydrofuran, was treated with boron trifluoride etherate to produce borane-THF complex (ca. 3060 GBq/mmol). (The maximum theoretical specific radioactivity of tritium is 1063 GBq/milliatom = 28.76 Ci/milliatom.) This complex was used in an exemplary reduction of 2-napthoic acid to 2-naphthalenemethanol, in high yield. Both the borane-THF complex and the reduction product were characterized by a combination of {sup 1}H, {sup 3}H, and {sup 11}B NMR techniques, as appropriate. The reduction product was found to have >94% of the maximum theoretical specific radioactivity, and all of the tritium at the reduced position. 2 figs.

• DOE Contract Number: AC03-76SF00098
• OSTI ID: 182235
• Journal Information: Journal of Organic Chemistry, Journal Name: Journal of Organic Chemistry Journal Issue: 23 Vol. 60; ISSN 0022-3263; ISSN JOCEAH
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
BORON COMPOUNDS
CHEMICAL PREPARATION
CHEMICAL REACTION YIELD
LABELLING
NUCLEAR MAGNETIC RESONANCE
TRITIUM COMPOUNDS