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Remote functionalization by tandem radical chain reactions

Wiedenfeld, David (1997) Remote functionalization by tandem radical chain reactions. Journal of the Chemical Society-Perkin Transactions 1, 1997 (3). pp. 339-347. ISSN 0300-922X. http://resolver.caltech.edu/CaltechAUTHORS:20120203-090344060

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Abstract

Normal radical relay chlorination of cholestan-3α-ol directed by an attached m-iodobenzoate ester group affords a 9α-chloro steroid, but when the same reaction is conducted in the presence of an excess of CBr4 the product is a 9α-bromo steroid. Similarly, when the same radical relay reaction is carried out in the presence of an excess of (SCN)_2 rather than CBr_4, the product is a 9α-thiocyano steroid. Several other examples of these reactions have been developed. These tandem remote functionalization reactions succeed because an intramolecular hydrogen abstraction by a complexed-chlorine atom generates a specific substrate radical in each case.


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http://dx.doi.org/10.1039/a600172f DOIUNSPECIFIED
http://pubs.rsc.org/en/Content/ArticleLanding/1997/P1/a600172fPublisherUNSPECIFIED
Additional Information:© 1997 by the Royal Society Chemistry. Received 8th January 1996. Accepted 2nd September 1996. Most of the described experiments were completed in the laboratories of Professor Ronald Breslow at Columbia University. Professor Breslow is gratefully acknowledged for helpful suggestions and encouraging submission of this manuscript. The National Institutes of Health supported this work. Dr Sonny Lee is gratefully acknowledged for growing crystals of 15 suitable for X-ray analysis and for his expertise in solving the X-ray data. Dr Joe Ziller collected the X-ray data at the UC Irvine facility. Dr Lars Skov made helpful suggestions during the revision and proofing of this manuscript.
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Record Number:CaltechAUTHORS:20120203-090344060
Persistent URL:http://resolver.caltech.edu/CaltechAUTHORS:20120203-090344060
Official Citation:Remote functionalization by tandem radical chain reactions David Wiedenfeld J. Chem. Soc., Perkin Trans. 1, 1997, 339-348 DOI: 10.1039/A600172F
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:29112
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:03 Feb 2012 17:40
Last Modified:26 Dec 2012 14:47

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