An unusual radical fragmentation of 8a-cycloalkenylmethyl Wieland-Miescher ketones mediated by tri-n-butyltin hydride

Rajamannar, Thennati ; Balasubramanian, Kalpattu Kuppusamy (1994) An unusual radical fragmentation of 8a-cycloalkenylmethyl Wieland-Miescher ketones mediated by tri-n-butyltin hydride Tetrahedron Letters, 35 (4). pp. 637-640. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4039(00)75858-8

Abstract

The behaviour of tri-n-butyltin hydride in poly functional molecule like Wieland-Miescher ketones, was found to be very unusual, a remarkable difference in chemoselectivity was noticed in the reductive cyclisation of cycloalkenyl bromides, resulting in the remote generation of the bromocyclopentenyl-methyl radical by a homolytic C-C bond cleavage.

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