Migratory insertion of bis(diethylamino)phosphine group into the N–N bond in the reaction of substituted hydrazobenzene with (Et2N)2PCl

Autor:	A. V. Sheyanova, E. V. Baranov, Yu. S. Panova, Alexander N. Kornev
Rok vydání:	2020
Předmět:	010405 organic chemistry Migratory insertion Hydrazine General Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry 0104 chemical sciences Dilithium chemistry.chemical_compound chemistry Methyllithium Dehydrogenation Diethyl ether Derivative (chemistry) Phosphine
Zdroj:	Russian Chemical Bulletin. 69:132-138
ISSN:	1573-9171 1066-5285
DOI:	10.1007/s11172-020-2734-6
Popis:	Oxidative dehydrogenation of 2-bromo-4-methylaniline with manganese(iv) oxide leads to the formation of (E)-1,2-bis(2-bromo-4-methylphenyl)diazene (1). The reaction of 1 with hydrazine hydrate gives the reduction product, 1,2-bis(2-bromo-4-methylphenyl)hydrazine (2). Compound 2 sequentially treated with methyllithium and two equivalents of (Et2N)2PCl in diethyl ether is converted to the diazadiphosphinine derivative. The reaction includes the following steps: 1) the phosphorylation of the nitrogen atom in the dilithium salt of hydrazo derivative 2, 2) the migratory insertion of (Et2N)2P group into the N–N bond, 3) phosphorylation of the second nitrogen atom, 4) arylation of the phosphorus in the (Et2N)2P group.
Databáze:	OpenAIRE
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