The formation of cage phosphoranes and their rearrangements in the reactions of substituted 2-(3-oxo-3-phenyl)ethoxybenzo[d]-1,3,2-dioxaphospholes with perfluorodiacetyl

Autor:	Vladimir F. Mironov, G. A. Ivkova, Igor A. Litvinov, Mudaris N. Dimukhametov, Daut R. Islamov, Khasan R. Khayarov
Rok vydání:	2021
Předmět:	Trifluoromethyl Chemistry Stereochemistry Metals and Alloys General Chemistry Phosphorane Catalysis Surfaces Coatings and Films Electronic Optical and Magnetic Materials D-1 chemistry.chemical_compound Materials Chemistry Ceramics and Composites Cage Derivative (chemistry)
Zdroj:	Chemical Communications. 57:8516-8519
ISSN:	1364-548X 1359-7345
DOI:	10.1039/d1cc02941j
Popis:	The Kukhtin–Ramirez reaction of 2-(3-oxo-3-phenyl)ethoxy-benzo[d]-1,3,2-dioxaphospholes with perfluorodiacetyl was monitored by NMR methods. To our surprise the initial stage involved a kinetically controlled [4+4]-cycloaddition with the formation of a cage phosphorane containing a 2′,5′,8′,9′-tetraoxa-2λ5-phosphaspiro[benzo[d][1,3,2]dioxaphosphole-2,1′-bicyclo[4.2.1]nonan]-3′-ene (compound 5) scaffold. Intermediate 5 then converts to spirophosphorane–4′,5′-bis(trifluoromethyl)-2λ5-spiro[benzo[d] [1,3,2]dioxaphosphole-2-yl-2,2′-[1,3,2] dioxaphosphole (compound 4). Compound 4 further rearranges into a cage phosphorane derivative containing a [2,5]epoxybenzo[d][1,3,6,2]trioxaphosphocine] (compound 3) backbone.
Databáze:	OpenAIRE
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