Abstract
Protonation of the reactive intermediate produced from the reaction between trialkyl phosphites and dimethyl acetylenedicarboxylate by ethyl carbazones of aromatic aldehydes following by conjugate addition of the anion of ethyl carbazone on the phosphonium salt intermediate leads to functionalised phosphonates in good yields. Triphenylphosphine also reacted with dimethyl acetylenedicarboxylate and ethyl carbazones to produce functionalised phosphoranes in good yields.
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References
1.
Engel R.
, Synthesis of carbon-phosphorus bonds , CRC Press , Boca Raton, FL , 1988 .
2.
Corbridge D.E. C.
, Phosphorus, an outline of chemistry, biochemistry and uses , 5th edn, Elsevier , Amsterdam , 1995 .
3.
Cadogan J.I. G.
, Organophosphorus reagents in organic synthesis , Academic Press , New York , 1979 .
4.
Johnson A.W.
,
Kaska W. C.
,
Starzewski A. O.
, and
Dixon K. D. A.
, Ylides and imines of phosphorus (John Wiley & Sons ), 1993 , pp. 386 –387 .
5.
Anary-abbasinejad M.
, and
Ascarrian N.
, J. Chem. Res. , 2007 , 11 .
6.
Anary-Abbasinejad M.
,
Hassanabadi A.
, and
Anaraki-Ardakani H.
, J. Chem. Res. , 2007 , 455 .
7.
Anary-Abbasinejad M.
,
Anaraki-Ardakani H.
, and
Hosseini-Mehdiabad H.
, Phosphorus, Sulfur, Silicon , 2008 , 183 , 6 , 1440.
8.
Hassanabadi A.
,
Anary-Abbasinejad M.
, and
Dehghan A.
, Synth. Commun. , 2009 , 39 , 1 , 132.
9.
Anary-Abbasinejad M.
,
Rostami N.
,
Parhami A.
, and
Hassanabadi A.
, J. Chem. Res. , 2007 , 257 .
10.
Anary-Abbasinejad M.
, and
Hassanabadi A.
, J. Chem. Res. , 2007 , 475 .
11.
Anary-Abbasinejad M.
,
Anaraki-Ardakani H.
,
Dehghan A.
,
Hassanabadi A.
, and
Seyedmir M. R.
, J. Chem. Res. , 2007 , 574 .
12.
Anary-Abbasinejad M.
,
Hassanabadi A.
, and
Mazraeh-Seffid M.
, J. Chem. Res. , 2007 , 708 .
13.
Karplus M.
, J. Am. Chem. Soc. , 1966 , 85 , 2870 .
14.
Haasnot C.A. G.
,
De Leeuww F. A. A. M.
, and
Altona C.
, Tetrahedron , 1980 , 36 , 2783 .
15.
Breitmaier E.
, and
Voelter W.
, Carbon-13 NMR spectroscopy 3rd edn., VCH , New York , 1990 , 250 .
16.
Tebby J.C.
, Phosphorus-31 NMR spectroscopy in Stereochemical Analysis ,
Verkade J.C.
,
Quin L. D.
, (Eds.); VCH : Weinheim , 1987 , chap. 1, pp. 1 –60 .
17.
Vedejs E.
, and
Snoble K. A. J.
, J. Am. Chem. Soc. , 1973 , 95 , 5778 .
