ORGANOPHOSPHORUS CHEMISTRY, 271. THE REACTION OF ISATIN, 5-METHYLISATIN AND THEIR MONOXIMES WITH ALKYL PHOSPHITES, TRIPHENYLPHOSPHINE AND PHOSPHORUS YLIDES

Autor:	Maha D. Khidre, Mohamed R. Mahran, Wafaa M. Abdou
Rok vydání:	1995
Předmět:	chemistry.chemical_classification Reaction mechanism Isatin Phosphorus Organic Chemistry chemistry.chemical_element Biochemistry Medicinal chemistry Inorganic Chemistry chemistry.chemical_compound chemistry Ylide Wittig reaction Proton NMR Organic chemistry Triphenylphosphine Alkyl
Zdroj:	Phosphorus, Sulfur, and Silicon and the Related Elements. 101:17-27
ISSN:	1563-5325 1042-6507
Popis:	5-Methylisatin ( 1b) reacts with TAP ( 4a–c) and/or DAP ( 3a-c) to give the respective dialkyl α-hydroxyphosphonates (8a-c). Isatin-monoxime ( 5a) and 5-methyl isatin-monoxime ( 5b) react with alkyl phosphites to give dialkyl 2-oxo-indolyl phosphorates ( 8a–c, 12a–f, 15a–c) as major products. The carbonyl-group at position – 3 in 1b is deoxygenated by triphenylphosphine to give a new phosphorus ylide ( 17 ) and by methylenetriphenylphosphoranes (Wittig-reagents, 7a-c) to afford the respective 3- substituted methylenes ( 19a-c) in good yields. Possible reaction mechanisms were considered and structural assignments were based upon analytical, chemical and spectroscopic (IR, 1H NMR, 31P NMR and MS) results.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::fdeccae6f7bbe0682dcad479c0d42ce0 https://doi.org/10.1080/10426509508042495 Zobrazit plný text záznamu