F. Ramirez, H. Kugler, C. P. Smith
1968
Citations
0
Influential Citations
6
Citations
Journal
Tetrahedron
Abstract
Abstract The tendency of certain nucleophiles to perform 1,2-additions to the CO group of p-quinones has been demonstrated. The nucleophile was 2,2,2-trimethoxy—4,5-dimethyl-2,2-dihydro-1,3,2-dioxaphospholene, made from biacetyl and trimethyl phosphite. The products of the 1,2-additions to p-benzoquinone and to 1,4-naphthoquinone were derivatives of the 2,2-dihydro-1,3,2-dioxaphospholane ring system with pentacovalent phosphorus. These pentaoxyphosphoranes were converted by one equivalent of water into biacetyl, methanol and the phosphate ester of the corresponding hydroquinone. Methanol induced a molecular rearrangement of the pentaoxyphosphoranes; the products were methyl acetate, trimethyl phosphate and the p-acetyl-phenols, i.e. acetophenone and 1-hydroxy-4-acetyl-naphthalene, respectively.