Reduction of Sulfur Dioxide and Carbon Dioxide with Benzoin Carbanion. Oxygen Transfer from Products Formed by the Reduction of Sulfur Dioxide to 7,7,8,8-Tetracyanoquinodimethane

Autor: Akiyama, Fuminori
Zdroj: Bulletin of the Chemical Society of Japan; November 1988, Vol. 61 Issue: 11 p3951-3955, 5p
Abstrakt: A reaction of sulfur dioxide (SO2) with benzoin carbanion (the lithium salt of benzoin dianion, 1) in tetrahydrofuran (THF) gave a mixture of benzil (2) and benzoin (3) in yields of 83 and 17%, respectively, irrespective of the reaction temperature between -78 and 25 °C. The reaction of carbon dioxide (CO2) with 1in THF gave a mixture of 2and 3accompanied by the formation of a small amount of lithium benzoate (4). The proportion of 2in a mixture of 2and 3formed in the reaction of CO2with 1were 49, 30, and 20% at -78, -22, and 25 °C, respectively. The reaction of SO2with 1in the presence of 7,7,8,8-tetracyanoquinodimethane (TCNQ) gave oligomers of TCNQ with a yield of 60%, in which some parts of the cyano groups were transformed to carboxylato groups.
Databáze: Supplemental Index