Photochemical Reactions of Chloranil with Cyclooctene, 1,5-Cyclooctadiene, and Cyclohexene Revisited

• Published in: European Journal of Organic Chemistry Vol. 2011; no. 5; pp. 968 - 982
• Main Authors: Christl, Manfred, Braun, Max, Deeg, Oliver, Wolff, Stephan
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.02.2011; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Chemistry; Chemistry, Organic; Cycloaddition; Dechlorination; Endiones; Exact sciences and technology; General and physical chemistry; Noncondensed benzenic compounds; Organic chemistry; Photochemistry; Physical chemistry of induced reactions (with radiations, particles and ultrasonics); Physical Sciences; Polycycles; Preparations and properties; Science & Technology; OXIDATION; Cycloaddition; Dechlorination; ELECTRON-TRANSFER; QUINONES; Endiones; PHOTOINDUCED REACTIONS; Polycycles; Photochemistry; PHOTOELECTRON-SPECTROSCOPY; Four membered ring; Quinone; Benzoquinone derivatives; Benzene derivatives; Asymmetric molecule; Polycyclic compound; Photochemical reaction; Ketone; Chemical reduction; Ultraviolet radiation; All cis stereoisomer; Bulb; Cyclobutane derivatives; Chloranil; Benzenic compound

Depending on the reaction conditions, excited chloranil (3CA) and cis‐cyclooctene (cis‐CO) furnished three types of products, which all contain carbocyclic four‐membered rings. The illumination of a solution in benzene by light bulbs gave rise to the all‐cis 1:1 cycloadduct (11a) in 76 % yield. On i...