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Synlett 2005(1): 59-62  
DOI: 10.1055/s-2004-836041
LETTER
© Georg Thieme Verlag Stuttgart · New York

Carbon-Carbon Bond Formation by Cyclization of Dienes Using Phosphorus-Centered Radicals in Water

Dae Hyan Choa, Doo Ok Jang*a,b
a Department of Chemistry, Yonsei University, Wonju 220-710, Korea
b Center for Bioactive Molecular Hybrids, Yonsei University, Seoul 120-749, Korea
Fax: +82(33)7602182; e-Mail: dojang@dragon.yonsei.ac.kr ;
Further Information

Publication History

Received 24 September 2004
Publication Date:
29 November 2004 (online)

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Abstract

An efficient and mild methodology for preparing carbocyclic and heterocyclic compounds with phosphorus functionality by radical cyclization of dienes in water without using organic co-solvents has been developed. The reaction affords environmentally benign reaction conditions.

Key words

radical - cyclization - water - diene - phosphorus hydride

11

Typical Reaction Procedure for Radical Addition-Cyclization Using Diphenylphosphine Oxide in Water: A mixture of 1,6-heptadiene (0.1 mL, 0.74 mmol), diphenylphosphine oxide (449 mg, 2.22 mmol,), CTAB (27 mg, 0.074 mmol) and ABCVA (71 mg, 0.19 mmol) in degassed H2O (10 mL) was heated to 80 °C under argon for 3 h. After the reaction was completed, the reaction mixture was diluted with EtOAc, then washed with H2O, dried over anhyd MgSO4, and the solvent was evaporated in vacuo. The residue was purified by flash column chromatography over silica gel (eluent: EtOAc) to give [(2-methylcyclo-pentyl)methyl]diphenylphosphine oxide (163 mg, 74%).