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Synthesis 2012(3): 460-468  
DOI: 10.1055/s-0031-1289998
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© Georg Thieme Verlag Stuttgart ˙ New York

Cyclic Aromatic Analogues of the Hendrickson Reagent; NMR Studies and Electrophilic Properties

Ziad Moussa*
Department of Chemistry, Taibah University, P.O. Box 30002, Almadinah Almunawarrah, Saudi Arabia
e-Mail: zmousa@taibahu.edu.sa ;
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Publikationsverlauf

Received 10 November 2011
Publikationsdatum:
22. Dezember 2011 (online)

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Cyclic Aromatic Analogues of the Hendrickson Reagent; NMR Studies and Electrophilic PropertiesSynthesis 2012; 44(03): e2-e2
DOI: 10.1055/s-0031-1289660

Abstract

Two novel cyclic aromatic analogues of the Hendrickson ‘POP’ reagent, 1,1,3,3-tetraphenyl-1,3-dihydro-2,1,3-benzoxadi­phosphole-1,3-diium bis(trifluoromethanesulfinate) and bis(tri­fluoromethanesulfonate), have been readily prepared by the treatment of 1,2-bis(diphenylphosphino)benzene or 1,2-bis(diphenyl­phosphoryl)benzene, respectively, with trifluoromethanesulfonic anhydride in dichloromethane. ³¹P and ¹9F NMR studies indicated that while the latter complex is formed as the sole product, the former species was shown to be the predominant component in equilibrium with 1-(diphenylphosphino)-2-[diphenyl(trifluorometh­ylsulfonyloxy)phosphonio]benzene trifluoromethanesulfinate and 1,2-bis[diphenyl(trifluoromethylsulfonyloxy)phosphonio]benzene bis(trifluoromethanesulfinate). The dehydrating ‘POP’ systems were exploited in the conversion of aldoximes into nitriles. The dehydration occurred rapidly at room temperature and produced high yields with a variety of alkyl- and arylaldoximes, tolerating a wide range of substrates and functional groups.

Key words

1,2-bis(diphenylphosphino)benzene - 1,2-bis(diphenylphosphoryl)benzene - trifluoromethanesulfonic anhydride - ­Hendrickson reagent - dehydration - aldoximes - nitriles

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