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

Dae Hyan Cho; Doo Ok Jang

doi:10.1055/s-2004-836041

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Synlett 2005(1): 59-62
DOI: 10.1055/s-2004-836041

LETTER

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

Dae Hyan Cho^a, 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)

Abstract
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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

References

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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%).