Abstract
Abstract 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 1 in THF gave a mixture of 2 and 3 accompanied by the formation of a small amount of lithium benzoate (4). The proportion of 2 in a mixture of 2 and 3 formed in the reaction of CO2 with 1 were 49, 30, and 20% at −78, −22, and 25 °C, respectively. The reaction of SO2 with 1 in 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.
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