Abstract
Protonation of the reactive 1:1 intermediate produced in the reaction between dialkyl acetylenedicarboxylates and triphenylphosphine by 3-(3,5-dimethyl pyrazol-1-yl)-3-oxopropionitrile leads to vinylphosphonium salts which undergo Michael addition with the conjugate base of the CH-acid to produce highly functionalised, salt-free phosphorus ylides in excellent yields.
References
1.
Engel R.
, Synthesis of carbon-phosphorus bonds , CRC Press , Boca Raton , 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.
Yavari I.
, and
Karimi E.
, Phosphorus, Sulfur Silicon Relat. Elem. , 2007 , 595 .
5.
Islami M.R.
,
Amrollahi M.A.
, and
Iranmanesh M.
, Arkivoc , 2009 , 35 .
6.
Alisadeh A.
,
Zohreh N.
, and
Zhu L.G.
, Synthesis , 2009 , 3 , 464 .
7.
Hassanabadi A.
,
Anary-Abbasinejad M.
, and
Dehghan A.
, Synth. Commun. , 2009 , 39 .
8.
Anary-Abbasinejad M.
,
Mosslemin M.H.
,
Hassanabadi A.
, and
Tabatabaee M.
, Synth. Commun. , 2008 , 38 , 3700 .
9.
Anary-Abbasinejad M.
,
Anaraki-Ardakani H.
, and
Hosseini-Mehdiabad H.
, Phosphorus, Sulfur Silicon Relat. Elem. , 2008 , 1440 .
10.
Anaraki-Ardakani H.
,
Sadeghian S.
,
Rastegari F.
,
Hassanabadi A.
, and
Anary-Abbasinejad M.
, Synth. Commun. , 2008 , 38 , 1990 .
11.
Anary-Abbasinejad M.
,
Anaraki-Ardakani H.
,
Dehghan A.
,
Hassanabadi A.
, and
Seyedmir M.R.
, J. Chem. Res. , 2007 , 574 .
12.
Anary-Abbasinejad M.
,
Anaraki-Ardakani H.
,
Ezadi A.
, and
Hassanabadi A.
, J. Chem. Res. , 2007 , 605 .
13.
Mosslemin M.H.
,
Anary-Abbasinejad M.
,
Hassanabadi A.
, and
Bagheri M.A.
, J. Sulfur, Chem. , 2010 , 31 , 135 .
14.
Tebby J.C.
, Phosphorus-31 NMR spectroscopy in stereochemical analysis;
Verkade J.C.
, and
Quin L.D.
(eds), VCH : Weinheim , 1987 , chap. 1, pp. 1 –60 .
15.
Vedejs E.
, and
Snoble K.A.J.
, J. Am. Chem. Soc. , 1973 , 95 , 5778 .
16.
Gorobets N.Y.
,
Yousefi B.H.
,
Belaj F.
, and
Kappe O.
, Tetrahedron , 2004 , 60 , 8633 .