Abstract
Ethyldiazoacetate reacts as a carbene precursor in presence of copper exchanged bentonite. Reaction with excess nitrile gave oxazole derivatives. Their formation is explained by intramolecular 1,5-cyclisation of alkoxycarbonyl substituted nitrile ylide intermediate.
Keywords
References
1.
Huisgen R.
,
Stangl H.
,
Sturm H.J.
, and
Wagenhofer H.
, Angew. Chem., Int. Ed. , 1962 , 1 , 50 .
2.
Steglich W.
,
Gruber P.
,
Ulrich H.H.
, and
Kneidl F.
, Chem. Ber. , 1971 , 104 , 3816 .
3.
Burger K.
,
Fehn J.
, and
Moll E.
, Chem. Ber. , 1971 , 104 , 1826 .
4.
Padwa A.
, and
Wetmore S.I.
Jr.
, J. Org. Chem. , 1974 , 39 , 1396 .
5.
Kende A.S.
,
Hebeisen P.
,
Sanfilippo P.J.
, and
Toder B.H.
, J. Am. Chem. Soc. , 1982 , 104 , 4244 .
6.
Doyle M.P.
, Chem. Rev. , 1986 , 86 , 919 .
7.
Saoudi A.
,
Hamelin J.
, and
Benhaoua H.
, J. Chem. Res. , 1996 , 492 .
8.
Hansen H.-J.
, and
Heimgartner H.
, 1,3-Dipolar cycloaddition chemistry , eds
Padwa A.
, John Wiley & Sons , New York , 1984 , Vol. 1 , pp. 177 –279 .
9.
Fukushima K.
, and
Ibata T.
, Bull. Chem. Soc. Jpn. , 1995 , 68 , 3469 .
10.
Caillère S.
,
Henin S.
, and
Rautureau M.
, Minéralogie des argiles , Ed. Masson , Paris , 1982 , Part 2, pp. 49 –56 .
11.
Adams J.M.
,
Ballantine J.A.
,
Graham S.H.
,
Laub R.J.
,
Purnell J.H.
,
Reid P.I.
,
Shaman W.Y.M.
, and
Thomas J.M.
, J. Catal. , 1979 , 58 , 238 .
12.
Elaziouti A.
,
Derriche Z.
,
Bouberka Z.
, and
Laouedj N.
, J. Korean Chem. Soc. , 2010 , 54 , 110 .
13.
Connell R.D.
,
Tebbe M.
,
Gangloff A.R.
,
Helquist P.
, and
Åkkermark B.
, Tetrahedron , 1993 , 49 , 5445 .
14.
Huang N.Y.
,
Nie Y.B.
, and
Ding M.W.
, Synlett , 2009 , 611 .
15.
McKay W.R.
, and
Proctor G.R.
, J. Chem. Soc., Perkin Trans. 1 , 1981 , 2443 .
16.
Kondratèwa G.Y.
, and
Tschshi-Chen K.
, Russ. J. Gen. Chem. , 1962 , 32 , 2315 .
17.
Zbiral E.
,
Bauer E.
, and
Stroh J.
, Monatsh. Chem. , 1971 , 102 , 168 .
18.
Shi B.
,
Blake A.J.
,
Campbell I.B.
,
Judkins B.D.
, and
Moody C.J.
, Chem. Commun. , 2009 , 3291 .
19.
Andersen T.P.
,
Ghattas A.G.
, and
Lawesson S.O.
, Tetrahedron , 1983 , 39 , 3419 .