An unusual cascade reaction of 4,5-dihydro-4,4-bis(trifluoromethyl)-2-phenyl-6,7-(4-chlorobenzo)[ e-1,3,2-dioxaphosphepin-5-one with chloral

The reaction of 4,5-dihydro-4,4-bis(trifluoromethyl)-2-phenyl-6,7-(4-chlorobenzo)[ e-1,3,2-dioxaphosphepin-5-one with chloral (1:2) proceeds with evolving hexafluoroacetone and gives spiro{2-oxo-4-trichloromethyl-4,5-dihydro-2-phenyl-6,7-(4-chlorobe n zo)[f]-1,3,2-dioxaphosphepine-5,2'-(3'...

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Published inMendeleev communications Vol. 20; no. 1; pp. 44 - 4644-46
Main Authors Mironov, Vladimir F, Borisova, Yuliya Yu, Burnaeva, Liliya M, Krivolapov, Dmitry B, Litvinov, Igor A, Zverev, Vladislav V, Musin, Rashid Z, Konovalova, Irina V
Format Journal Article
LanguageEnglish
Published 01.02.2010
Subjects
Cascades
Chloral
Diffraction
Single crystals
Stereoselectivity
X-rays
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Summary:The reaction of 4,5-dihydro-4,4-bis(trifluoromethyl)-2-phenyl-6,7-(4-chlorobenzo)[ e-1,3,2-dioxaphosphepin-5-one with chloral (1:2) proceeds with evolving hexafluoroacetone and gives spiro{2-oxo-4-trichloromethyl-4,5-dihydro-2-phenyl-6,7-(4-chlorobe n zo)[f]-1,3,2-dioxaphosphepine-5,2'-(3'-trichloromethyl)oxirane} with a high stereoselectivity. Configuration of the four chiral centres (P super(2) sub(S)C super(4) sub(S)C super(5) sub(S)C super(3') sub(S) /P super(2) sub(R)C super(4) sub(R)C super(5) sub(R)C super(3') sub(R)) was determined by a single crystal X-ray diffraction.
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ISSN:0959-9436
DOI:10.1016/j.mencom.2010.01.017