-
1
-
-
53549128637
-
-
For a recent review on the synthesis of azetidines and azetidinones, see : A. Brandi, S. Cicchi, F. M. Cordero, Chem. Rev. 2008, 108, 3988-4035.
-
(2008)
Chem. Rev.
, vol.108
, pp. 3988-4035
-
-
Brandi, A.1
Cicchi, S.2
Cordero, F.M.3
-
2
-
-
48249121520
-
-
S. Mangelinckx, V. Van Speybroeck, P. Vansteenkiste, M. Waroquier, N. De Kimpe, J. Org. Chem. 2008, 73, 5481-5488.
-
(2008)
J. Org. Chem.
, vol.73
, pp. 5481-5488
-
-
Mangelinckx, S.1
Van Speybroeck, V.2
Vansteenkiste, P.3
Waroquier, M.4
De Kimpe, N.5
-
5
-
-
0028237134
-
-
c) A. P. Marchand, D. Rajagopal, S. G. Bott, T. G. Archibald, J. Org. Chem. 1994, 59, 1608-1612;
-
(1994)
J. Org. Chem.
, vol.59
, pp. 1608-1612
-
-
Marchand, A.P.1
Rajagopal, D.2
Bott, S.G.3
Archibald, T.G.4
-
6
-
-
0032581655
-
-
d) P. R. Dave, R. Duddu, J. Li, R. Surapaneni, R. Gilardi, Tetrahedron Lett. 1998, 39, 5481-5484;
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 5481-5484
-
-
Dave, P.R.1
Duddu, R.2
Li, J.3
Surapaneni, R.4
Gilardi, R.5
-
8
-
-
0011813026
-
-
a) The isolation of dimethyl 1-ethyl-4-methyl-2-azetine-2,3-dicarboxylate in 9% yield has been reported; see: E. Winterfeldt, W. Krohn, Chem. Ber. 1969, 102, 2336-2345;
-
(1969)
Chem. Ber.
, vol.102
, pp. 2336-2345
-
-
Winterfeldt, E.1
Krohn, W.2
-
10
-
-
0037023473
-
-
Typical procedure involves the multistep synthesis of a suitable azetidine precursor, followed by elimination; a) see Ref. [2,3b,d,e]; b) Y. Dejaegher, S. Mangelinckx, N. De Kimpe, J. Org. Chem. 2002, 67, 2075-2081.
-
(2002)
J. Org. Chem.
, vol.67
, pp. 2075-2081
-
-
Dejaegher, Y.1
Mangelinckx, S.2
De Kimpe, N.3
-
13
-
-
0001044209
-
-
H. Ishitani, S. Nagayama, S. Kobayashi, J. Org. Chem. 1996, 61, 1902-1903.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 1902-1903
-
-
Ishitani, H.1
Nagayama, S.2
Kobayashi, S.3
-
14
-
-
0007143067
-
-
R. Aumann, Z. Yu, R. Froehlich, F. Zippel, Eur. J. Inorg. Chem. 1998, 1623-1629.
-
(1998)
Eur. J. Inorg. Chem.
, pp. 1623-1629
-
-
Aumann, R.1
Yu, Z.2
Froehlich, R.3
Zippel, F.4
-
15
-
-
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-
-
For recent results from our research group involving nonheteroatom- stabilized alkynycarbene complexes, see: a) J. Barluenga, P. García-García, D. de Sáa, M. A. Fernández- Rodríguez, R. Bernardo de La Rúa, A. Ballesteros, E. Aguilar, M. Tomás, Angew. Chem. 2007, 119, 2664-2666;
-
(2007)
Angew. Chem.
, vol.119
, pp. 2664-2666
-
-
Barluenga, J.1
García-García, P.2
De Sáa, D.3
Fernández-Rodríguez, M.A.4
Bernardo De La Rúa, R.5
Ballesteros, A.6
Aguilar, E.7
Tomás, M.8
-
16
-
-
34250806562
-
-
Angew. Chem. Int. Ed. 2007, 46, 2610-2612;
-
(2007)
Angew. Chem. Int. Ed.
, vol.46
, pp. 2610-2612
-
-
-
17
-
-
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-
b) J. Barluenga, D. de Sáa, A. Gómez, A. Ballesteros, J. Santamaría, A. de Prado, M. Tomás, A. L. Suarez-Sobrino, Angew. Chem. 2008, 120, 6321-6324;
-
(2008)
Angew. Chem.
, vol.120
, pp. 6321-6324
-
-
Barluenga, J.1
De Sáa, D.2
Gómez, A.3
Ballesteros, A.4
Santamaría, J.5
De Prado, A.6
Tomás, M.7
Suarez-Sobrino, A.L.8
-
18
-
-
51649106855
-
-
Angew. Chem. Int. Ed. 2008, 47, 6225-6228;
-
(2008)
Angew. Chem. Int. Ed.
, vol.47
, pp. 6225-6228
-
-
-
19
-
-
70350070380
-
-
c) J. Barluenga, A. Gómez, J. Santamaría, M. Tomás, J. Am. Chem. Soc. 2009, 131, 14628-14629.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 14628-14629
-
-
Barluenga, J.1
Gómez, A.2
Santamaría, J.3
Tomás, M.4
-
20
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-
0001223326
-
-
For recent reviews, see: a) A. de Meijere, H. Schirmer, M. Duetsch, Angew. Chem. 2000, 112, 4124-4162;
-
(2000)
Angew. Chem.
, vol.112
, pp. 4124-4162
-
-
De Meijere, A.1
Schirmer, H.2
Duetsch, M.3
-
21
-
-
0000036185
-
-
Angew. Chem. Int. Ed. 2000, 39, 3964-4002;
-
(2000)
Angew. Chem. Int. Ed.
, vol.39
, pp. 3964-4002
-
-
-
23
-
-
0034301372
-
-
c) M. A. Sierra, Chem. Rev. 2000, 100, 3591-3637;
-
(2000)
Chem. Rev.
, vol.100
, pp. 3591-3637
-
-
Sierra, M.A.1
-
25
-
-
2942609170
-
-
e) J. Barluenga, J. Santamaría, M. Tomás, Chem. Rev. 2004, 104, 2259-2283;
-
(2004)
Chem. Rev.
, vol.104
, pp. 2259-2283
-
-
Barluenga, J.1
Santamaría, J.2
Tomás, M.3
-
26
-
-
13644249943
-
-
f) J. Barluenga, M. A. Fernández-Rodríguez, E. Aguilar, J. Organomet. Chem. 2005, 690, 539-587;
-
(2005)
J. Organomet. Chem.
, vol.690
, pp. 539-587
-
-
Barluenga, J.1
Fernández-Rodríguez, M.A.2
Aguilar, E.3
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The azetines 5 are stable when stored under nitrogen at 0-20°C.
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The azetines 5 are stable when stored under nitrogen at 0-20°C.
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3 = Ph) is employed, the expected azetine was not formed, but a [4+3] cyclization was observed wherein the phenylimine behaves as the 1-azadiene unit.
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3 = Ph) is employed, the expected azetine was not formed, but a [4+3] cyclization was observed wherein the phenylimine behaves as the 1-azadiene unit.
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2 ≠ Fc) are used, undergo a [3+3] cyclization reaction to afford benzofurans; see Ref. [10c].
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2 ≠ Fc) are used, undergo a [3+3] cyclization reaction to afford benzofurans; see Ref. [10c].
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The reaction of the tungsten azetine complex 5g with paratolylacetylene formed a complex mixture rather than the expected cycloadduct 7b.
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The reaction of the tungsten azetine complex 5g with paratolylacetylene formed a complex mixture rather than the expected cycloadduct 7b.
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For a sequence involving initial insertion of two alkyne units and carbon monoxide into a Fischer alkenyl carbene, followed by nucleophilic cyclization,see: F. Stein, M. Duetsch, R. Lackmann, M. Noltemeyer, A. de Meijere, Angew. Chem. 1991, 103, 1669-1671;
-
(1991)
Angew. Chem.
, vol.103
, pp. 1669-1671
-
-
Stein, F.1
Duetsch, M.2
Lackmann, R.3
Noltemeyer, M.4
De Meijere, A.5
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a) For a rare example of the formation of a 1-azetinium salt from the [2+2] cycloadditon of a nitrilium salt and methyleneadamantane, see: A. H. Moustafa, W. Wirschun, C. C. Freyhardt, J. C. Jochims, R. Abu-El-Halawa, J. Prakt. Chem. 1997, 339, 615-622;
-
(1997)
J. Prakt. Chem.
, vol.339
, pp. 615-622
-
-
Moustafa, A.H.1
Wirschun, W.2
Freyhardt, C.C.3
Jochims, J.C.4
Abu-El-Halawa, R.5
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b) it is well established that vinyl or allylammonium salts undergo the [3,3] rearrangement faster than their uncharged parent allylenamines; see: K. C. Majumdar, T. Bhattacharyya, B. Chattopadhyay, B. Sinha, Synthesis 2009, 2117-2142.
-
(2009)
Synthesis
, pp. 2117-2142
-
-
Majumdar, K.C.1
Bhattacharyya, T.2
Chattopadhyay, B.3
Sinha, B.4
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