RADICAL CYCLISATION OF 1-BROMO-2-(PROP-2-ENYLOXY)BENZENE USING A POLYMER-SUPPORTED ORGANOTIN HYDRIDE

The use of polymer-supported organotin hydride for the cyclisation 1-bromo-2-(prop-2-enyloxy)benzene I to give 2,3-dihydro-3-methylbenzofuran II has been studied. The supports were prepared by suspension copolymerisation of an organotin-functionalised monomer. Two approaches have been investigated either using a stoichiometric or a catalytic amount of organotin support.

[1]  Sabine Hadida,et al.  Fluorous tin hydrides: A new family of reagents for use and reuse in radical reactions , 1999 .

[2]  A. Chemin,et al.  Preparation and reactivity of a macroporous polymer-supported organotin hydride catalyst , 1998 .

[3]  John C. Walton Homolytic Substitution: A Molecular Ménage à Trois , 1998 .

[4]  W. Neumann,et al.  An improved synthesis of a polymer-supported distannane and its application to radical formation , 1997 .

[5]  D. Crich,et al.  A Practical Method for the Removal of Organotin Residues from Reaction Mixtures. , 1996, The Journal of organic chemistry.

[6]  O. Donard,et al.  Towards non-polluting organotin reagents for synthesis , 1995 .

[7]  W. Neumann,et al.  Tin for organic synthesis, part 9 , 1993 .

[8]  B. Delmond,et al.  Un nouvel hydrure organostannique greffé sur support insoluble , 1993 .

[9]  W. Motherwell,et al.  Free Radical Chain Reactions in Organic Synthesis , 1992 .

[10]  H. Koller,et al.  2,3-Dihydro-7-benzofurancarbonsäuren , 1990 .

[11]  P. G. Harrison Chemistry of tin , 1989 .

[12]  D. Curran,et al.  Atom transfer cyclization reactions of .alpha.-iodo esters, ketones, and malonates: examples of selective 5-exo, 6-endo, 6-exo, and 7-endo ring closures , 1989 .

[13]  W. Neumann Tri-n-butyltin Hydride as Reagent in Organic Synthesis , 1988 .

[14]  A. Beckwith,et al.  Consecutive ring closure and neophyl rearrangement of some alkenylaryl radicals , 1987 .

[15]  E. Corey,et al.  Method for catalytic dehalogenations via trialkyltin hydrides , 1975 .

[16]  A. Chemin,et al.  Preparation and reactivity of a non-styrenic polymer-supported organotin chloride catalyst , 1999 .

[17]  J. Fréchet,et al.  New solid-phase catalysts for asymmetric synthesis: cross-linked polymers containing a chiral Schiff base-zinc complex , 1990 .

[18]  E. S. Huyser Free-radical chain reactions , 1970 .