Published February 7, 1997
| Published
Journal Article
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Remote functionalization by tandem radical chain reactions
- Creators
- Wiedenfeld, David
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.
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.Attached Files
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Additional details
- Eprint ID
- 29112
- Resolver ID
- CaltechAUTHORS:20120203-090344060
- NIH
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2012-02-03Created from EPrint's datestamp field
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2021-11-09Created from EPrint's last_modified field