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
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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 H2 O (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 H2 O, 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%).
