Reductive alkylation of p-benzoquinone using mixed organoboranes |
| |
Authors: | David J Zillman |
| |
Institution: | Department of Chemistry and Biochemistry, San Diego State University, San Diego, CA 92182-1030, United States |
| |
Abstract: | Mixed organoboranes based on diphenyl- or dimethylalkylboranes transfer the alkyl group in the reductive alkylation of p-benzoquinone to form the alkylhydroquinones in very high yields. The auxiliary groups do not transfer or have a low migratory aptitude. Primary and secondary alkyl groups are transferred with retention of regio- and stereochemistry to the hydroquinone. O-Alkylation is the major product with tertiary and secondary groups with steric bulk in proximity to the site of attachment. The presence of metal salts, such as magnesium, results in reduction to the unsubstituted hydroquinone. This reaction makes the first practical route to alkylhydroquinones via organoboranes. |
| |
Keywords: | p-Benzoquinone Hydroquinones Reductive alkylation Organoboranes Alkyldimethylboranes |
本文献已被 ScienceDirect 等数据库收录! |
|