FREE RADICAL DESULFENYLATION AND DESELENYLATION OF α-SULFUR AND α-SELENO SUBSTITUTED PHOSPHONATES WITH THEn-Bu3SnH/AIBN REAGENTS SYSTEM1
- 1 July 1995
- journal article
- research article
- Published by Taylor & Francis in Phosphorus, Sulfur, and Silicon and the Related Elements
- Vol. 104 (1-4) , 113-121
- https://doi.org/10.1080/10426509508042583
Abstract
Selective desulfenylation and deselenylation of α-sulfur- and α-seleno-substituted phosphonates under free radical conditions are described. Chemoselectivity and scope of the title reactions were studied using phosphonates additionally functionalized in the α-position by alkyl, phenyl, ethoxy, chloro, car-bonyl and sulfenyl groups. It was found that reduction of a halogen tolerates the presence of the sulfenyl group and the latter could be reduced in the presence of the sulfinyl and sulfonyl moieties. Moreover, one sulfenyl group was selectively removed from α-phosphoryl dithioacetals and the phenylsulfenyl group was reduced preferentially in the presence of the methylsulfenyl one.Keywords
This publication has 14 references indexed in Scilit:
- Intermolecular radical displacement reactions of heteroaromatic aryl sulphonesTetrahedron Letters, 1993
- The invention of radical reactions. Part XXIX. Radical mono- and dideoxygenations with silanesTetrahedron, 1993
- Synthesis of 1-diethoxyphosphoryl-1-methylthio-thioacetamides and 1-methylthioethenethioamides. An unusual intramolecular α-desulfenylation of thioacetamidesTetrahedron, 1993
- A General Synthesis of Dialkyl 1-(Triorganostannyl)alkylphosphonatesSynthesis, 1991
- Radical addition to vinyl phosphonates. A new synthesis of isosteric phosphonates and phosphonate analogues of α-amino acidsJournal of the Chemical Society, Chemical Communications, 1989
- Synthesis of five-membered lactams by α-carbamoyl radical cyclisationsJournal of the Chemical Society, Perkin Transactions 1, 1989
- Synthesis of a difluoromethylenephosphonate analogue of glycerol-3-phosphate. A substrate for NADH linked glycerol-3-phosphate dehydrogenaseJournal of the Chemical Society, Chemical Communications, 1988
- Pyrrolizidinone and indolizidinone synthesis: generation and intramolecular addition of .alpha.-acylamino radicals to olefins and allenesJournal of the American Chemical Society, 1984
- Sulphenylation of Phosphonates. A Facile Synthesis of α-Phosphoryl Sulphides andS,S-Acetals of OxomethanephosphonatesSynthesis, 1980
- α‐Substituierte Phosphonate. XXIII. Synthese offenkettiger und cyclischer S,S‐Acetale von FormylphosphonsäureesternJournal für Praktische Chemie, 1977