Structures of two major products in hypoiodite reaction of 3α- and 3β-hydroxy-Δ5-steroids. A correction.

✍ Scribed by Hiroshi Suginome; Akio Furusaki; Kimitoshi Kato; Takeshi Matsumoto

• Publisher: Elsevier Science
• Year: 1975
• Tongue: French
• Weight: 207 KB
• Volume: 16
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)75232-4

✦ Synopsis

In our recent paper 2 it was reported that the photoinduced hypoiodite reaction of cholesterol (1) or epicholesterol (2) with HgO and I2 in benzene under an argon atmosphere afforded two iodine-containing products ( 3) and ( 4)

and 4-iodo-3,4-seco-cholest-5-en-3 al (5). Oxidomethylene-3a,5a-A-norcholestane structures (A) and (B) were proposed for these iodine-containing products on the basis of the 1 H n.m.r. and the spin-decoupling experiments of these compounds and the D-incorporated compounds as well as consideration of probable mechanistic pathways of their formation.

In this paper we wish to report that the proposed structures for these two compounds are not correct and