ChemInform Abstract: An Investigation of the Yang Photocyclization Reaction in the Solid State: Asymmetric Induction Studies and Crystal Structure—Reactivity Relationships.

✍ Scribed by Mordechai Leibovitch; Gunnar Olovsson; John R. Scheffer; James Trotter

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 30 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199915058

✦ Synopsis

An Investigation of the Yang Photocyclization Reaction in the Solid State: Asymmetric Induction Studies and Crystal Structure-Reactivity Relationships. -In contrast to solid-state chemical reactions of nonionic crystals, which have to be carried out at low temp. and to low conversions, analogous processes of ionic crystals are carried out to much higher conversions without significant loss of topochemical control. The successful application of solid-state photochemistry of salts in which one of the ions is a chiral auxiliary as general method to asymmetric induction in the well-known Yang photocyclization reaction -the photochemical conversion of γ-hydrogencontaining carbonyl compounds into cyclobutanols -is described. Further penetrating insights into details of Norrish/Yang type II reaction are given, including the stereoelectronic requirements for γ-hydrogen abstraction and 1,4-biradical ring closure. -(LEIBOVITCH, MORDECHAI; OLOVSSON,