Abstract
5-Oxo-1,2λ5-oxaphospholane derivatives were obtained in excellent yields from the reaction between alkyl or aryl phosphines, and itaconic anhydride in presence of water in dichloromethane.
References
1.
Mathey F.
, Phosphorous-Carbon Heterocyclic Chemistry: The Rise of a New Domain ; Pergamon , Amsterdam , 2001 .
2.
Engel R.
, Synthesis of Carbon-Phosphorus Bonds ; CRC Press , Boca Raton, FL , 1998 .
3.
(a)
Hanessian S.
, and
Rogel O.
, J. Org. Chem. , 2000 , 65 , 2667 .
4.
Hanessian S.
, and
Rogel O.
, Bioorg. Med. Chem. Lett. , 1999 , 9 , 2441 .
5.
Harvey T.C.
,
Simiand C.
,
Weiler L.
, and
Withers S. G.
, J. Org. Chem. , 1997 , 62 , 6722 .
6.
Balabanovich A.I.
,
Balabanovich A. M.
, and
Engelmann J.
, Polym. Int. , 2003 , 52 , 1309 .
7.
Balabanovich A.I.
, Thermochimica Acta , 2004 , 409 , 33 .
8.
Hands A.R.
, and
Mercer A. J. H.
, J. Chem. Soc. , C 1967 , 1099 .
9.
(a)
Ramirez F.
,
Pilot J. F.
,
Madan P.
, and
Smith C. P.
, J. Am. Chem. Soc. , 1968 , 90 , 1275 .
10.
Enholm E.J.
,
Satici H.
, and
Prasad G.
, J. Org. Chem. , 1990 , 55 , 324 .
11.
Okuma K.
,
Tanaka Y.-I.
,
Hirabayashi S.-I.
,
Shioji K.
, and
Matsuyama H.
, Heterocycles , 1997 , 45 , 1385 .
12.
Okuma K.
,
Himbayashi S.-I.
,
Ono M.
,
Shioji K.
,
Matsuyama H.
, and
Bestmann H. J.
, Tetrahedron , 1998 , 54 , 4243 .
13.
Bujard M.
,
Gouverneur V.
, and
Mioskowski C.
, J. Org. Chem. , 1999 , 64 , 2119 .
14.
Timmer M.S. M.
,
Ovaa H.
,
Filippov D. V.
,
van der Marel G. A.
, and
van Boom J. H.
, Tetrahedron Lett. , 2001 , 42 , 8231 .
15.
Stoianova D.S.
, and
Hanson P. R.
, Org. Lett. , 2001 , 3 , 3285 .
16.
Hetherington L.
,
Greedy B.
, and
Gouverneur V.
Tetrahedron , 2000 , 56 , 2053 .
17.
Yavari I.
,
Alizadeh A.
, and
Anary-Abbasinejad M.
, Tetrahedron Lett. , 2003 , 44 , 2877 .
18.
Hah J.H.
,
Lee B. S.
,
Lee S. Y.
, and
Lee H.-Y.
, Tetrahedron Lett. , 2003 , 44 , 5811 .
19.
McReynolds M.D.
,
Dougherty J. M.
, and
Hanson P. R.
, Chem. Rev. , 2004 , 104 , 2239 and references cited therein.
20.
(a)
Shaabani A.
,
Teimouri M. B.
,
Yavari I.
,
Norouzi Arasi H.
, and
Bijanzadeh H. R
, J. Fluorine Chem. , 2000 , 103 , 155 .
21.
Shaabani A.
,
Bazgir A.
, and
Teimouri M. B.
, Phosphorus Sulfur Silicon , 2002 , 177 , 833 .
22.
Kolodiazhynyi O.I.
, Russ. Chem. Rev. , 1997 , 66 , 225 .
23.
Bestmann H.J.
, and
Vostrowsky O.
, Top. Curr. Chem. , 1983 , 109 , 85 .
24.
Pietrusiewiz K.M.
, and
Zabloka M.
, Chem. Rev. , 1994 , 94 , 1375 .
25.
Karplus M.
, J. Am. Chem. Soc. , 1963 , 85 , 2870 .