Synthesis of 1,4-dihydrophosphinoline 1-oxides by acid-promoted cyclization of 1-(diphenylphosphoryl)allenes

Autor:	Alexander S. Bogachenkov, Vadim P. Boyarskiy, Aleksander V. Vasilyev, Albina V. Dogadina, Irina A. Boyarskaya
Rok vydání:	2016
Předmět:	Hydrolysis 010405 organic chemistry Chemistry Organic Chemistry Organic chemistry Lewis acids and bases Physical and Theoretical Chemistry 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Ion
Zdroj:	Organic & Biomolecular Chemistry. 14:1370-1381
ISSN:	1477-0539 1477-0520
DOI:	10.1039/c5ob02143j
Popis:	1-(Diphenylphosphoryl)alka-1,2-dienes (phosphonoallenes) in Brønsted (super)acids (TfOH, FSO3H, H2SO4) gave the corresponding 1,2-oxaphosphol-3-enium ions, that were studied by means of NMR and DFT calculations. Upon hydrolysis of reaction solution, these cations afforded 3-hydroxyalk-2-en-1-yl-diphenylphosphine oxides (phosphonoallyl alcohols). But in (super)acids the cations were slowly transformed into O-protonated forms of 1-phenyl-1,4-dihydrophosphinoline 1-oxides, which were monitored by NMR. The latter phosphaheterocycles can be directly obtained from phosphonoallenes under the action of Lewis acid AlCl3.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ba62d7311a07c5132499c876b3597ee1 https://doi.org/10.1039/c5ob02143j Zobrazit plný text záznamu