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Communication | Special issue | Vol 28, No. 1, 1989, pp.23-28
Published online, 1st January, 1970
DOI: 10.3987/COM-88-S8
The Radical Relay Chlorination of Fleible Nicotinate Esters

Radhika Batrd and Ronald Breslow*

*Department of Chemistry, Columbia University, 3000 Broadway, Mail Code 3114, New York, New York 10027, U.S.A.


Dodecyl and hexadecyl nicotinates undergo radical relay chlorination with selectivities consistent with molecular models and with results in steroids. Alternating effects are seen, reflecting straight-chain conformations. A novel sequence for product analysis is validated, and used to compare the nicotinate template, and its N-oxide, with previously studied iodoaryl templates.