ORGANOPHOSPHORUS COMPOUNDS, XXXII THE REACTION OF ALKYL PHOSPHITES WITH 1-(DIPHENYLMETHYLENE)-2(1H)- AND 4-(DIPHENYLMETHYLENE)-1(4H)-NAPHTHALENONES
- 1 August 1981
- journal article
- research article
- Published by Taylor & Francis in Phosphorus and Sulfur and the Related Elements
- Vol. 10 (3) , 343-347
- https://doi.org/10.1080/03086648108077386
Abstract
1-(Diphenylmethylene)-2(1H)-naphthalenone (1) reacts with trialkyl phosphites to give the corresponding 1,2-dihydro-2-alkoxy-1,1-diphenylnaphth[1,2-d-] [1,2]-oxaphosphole-2-oxides (3a-c). The latter compounds are equally obtained by the reaction of dialkyl phosphites with 1. A mechanism for this reaction is presented which accounts for the experimental results. On the other hand, 4-(diphenylmethylene)-1(4H)-naphthalenone (2) reacts only with dialkyl phosphites to give dialkyl[4-diphenylmethylene)-1,4-dihydro-1-hydroxy-1-naphthyl]-phosphonates (9a-c). Structural assignments are based on analytical, chemical and spectroscopic evidence.Keywords
This publication has 10 references indexed in Scilit:
- Crystal and molecular structure of phosphate esters. 9. Crystal and molecular structure of o-hydroxyphenyl-o-phenylene phosphate, (o-HOC6H4)(C6H4)PO4. Equilibrium between pentavalent and tetravalent phosphorus in solutionsJournal of the American Chemical Society, 1978
- Organophosphorus compounds. XXI. The Reaction of Alkyl Phosphites with 10‐Methyleneanthrone and 10‐ArylideneanthronesJournal für Praktische Chemie, 1974
- Reaction of a quinone methide with triethyl phosphiteThe Journal of Organic Chemistry, 1969
- Formation of phosphorus-oxygen bonds in the reactions of triaminophosphines with o-quinones, vicinal triketones, and xoxmalonic esters. Triaminooxyphosphonium dipolar ions and triaminodioxaphosphoranes. Phosphorus-31 nuclear magnetic resonance spectraJournal of the American Chemical Society, 1967
- Reaction of di- and trialkyl phosphites with isatinsTetrahedron, 1966
- Reaction of Triaminophosphines with Oxomalonic Esters, Vicinal Triketones, and o-Quinones. Triaminooxyphosphonium Dipolar Ions1Journal of the American Chemical Society, 1965
- Kinetics and Mechanisms of the Rapid Alkaline Hydrolysis of Dimethyl PhosphoacetoinJournal of the American Chemical Society, 1962
- Esters containing phosphorus—XVITetrahedron, 1958
- TRIETHYL PHOSPHITEOrganic Syntheses, 1951
- TAUTOMERISM IN THE TRIARYL CARBINOL SERIES; DIPHENYL-4-HYDROXY-1-NAPHTHYL CARBINOL AND DIPHENYL-2-HYDROXY-1-NAPHTHYL CARBINOL.Journal of the American Chemical Society, 1920