96043-76-4

Upstream product

• 57498-63-2 Cholestan-3α-yl 4'-iodobiphenyl-3-carboxylate 
• 77546-99-7 4'-Iodo-biphenyl-3-carboxylic acid (3R,5S,8R,9S,10S,13S,14S,17S)-17-chloro-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 

Relevant academic research and scientific papers

Remote functionalization by tandem radical chain reactions

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 CBr4, 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. Copyright 1997 by the Royal Society Chemistry.

UNUSUAL STRUCTURAL EFFECTS ON THE CHEMICAL DEGRADATION OF STERIOD SIDECHAINS1

17-Chlorosteroids from template-directed halogenation can be converted to 17(20) olefins with BDU or DBN.The dependence of this reaction on base-structure and reaction conditions suggests geometric control by liquid packing effects related to those operating in liquid crystals.