-
3
-
-
77954843118
-
-
For accounts and reviews on the reactivity of transient sila-ylides, see: a) K. Tamao, M. Asahara, T. Saeki, A. Toshimitsu; T. Saeki, K. Tamao, J. Am. Chem. Soc. 2001, 123, 9210-9211,
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 9210-9211
-
-
Tamao, K.1
Asahara, M.2
Saeki, T.3
Toshimitsu, A.4
Saeki, T.5
Tamao, K.6
-
4
-
-
0000645550
-
-
J. Organomet. Chem. 2000, 600, 118-123;
-
(2000)
J. Organomet. Chem.
, vol.600
, pp. 118-123
-
-
-
5
-
-
0000220312
-
-
b) K. Tamao, A. Kawachi, M. Asahara, A. Toshimitsu, Pure Appl. Chem. 1999, 71, 393;
-
(1999)
Pure Appl. Chem.
, vol.71
, pp. 393
-
-
Tamao, K.1
Kawachi, A.2
Asahara, M.3
Toshimitsu, A.4
-
6
-
-
0036020762
-
-
c) A. Toshimitsu, T. Saeki, K. Tamao, Phosphorus Sulfur Silicon Relat. Elem. 2002, 177, 1409.
-
(2002)
Phosphorus Sulfur Silicon Relat. Elem.
, vol.177
, pp. 1409
-
-
Toshimitsu, A.1
Saeki, T.2
Tamao, K.3
-
7
-
-
33746280729
-
-
a) C. W. So, H. W. Roesky, J. Magull, E. B. Oswald, Angew. Chem. 2006, 118, 4052;
-
(2006)
Angew. Chem.
, vol.118
, pp. 4052
-
-
So, C.W.1
Roesky, H.W.2
Magull, J.3
Oswald, E.B.4
-
9
-
-
34848848440
-
-
b) C. W. So, H. W. Roesky, P. M. Gurubasavaraj, R. B. Oswald, M. T. Gamer, P. G. Jones, S. Blaurock, J. Am. Chem. Soc. 2007, 129, 12049.
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 12049
-
-
So, C.W.1
Roesky, H.W.2
Gurubasavaraj, P.M.3
Oswald, R.B.4
Gamer, M.T.5
Jones, P.G.6
Blaurock, S.7
-
10
-
-
70350720510
-
-
a) R. S. Ghadwal, H. W. Roesky, S. Merkel, J. Henn, D. Stalke, Angew. Chem. 2009, 121, 5793;
-
(2009)
Angew. Chem.
, vol.121
, pp. 5793
-
-
Ghadwal, R.S.1
Roesky, H.W.2
Merkel, S.3
Henn, J.4
Stalke, D.5
-
12
-
-
70350722897
-
-
b) A. C. Filippou, O. Chernov, G. Schnakenburg, Angew. Chem. 2009, 121, 5797;
-
(2009)
Angew. Chem.
, vol.121
, pp. 5797
-
-
Filippou, A.C.1
Chernov, O.2
Schnakenburg, G.3
-
14
-
-
41149155364
-
-
c) S. Yao, M. Brym, C. van Wüllen, M. Driess, Angew. Chem. 2007, 119, 4237;
-
(2007)
Angew. Chem.
, vol.119
, pp. 4237
-
-
Yao, S.1
Brym, M.2
Van Wüllen, C.3
Driess, M.4
-
16
-
-
0030901326
-
-
a) N. Takeda, H. Suzuki, N. Tokitoh, R. Okazaki, J. Am. Chem. Soc. 1997, 119, 1456;
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 1456
-
-
Takeda, N.1
Suzuki, H.2
Tokitoh, N.3
Okazaki, R.4
-
17
-
-
0042031213
-
-
b) N. Takeda, T. Kajiwara, H. Suzuki, R. Okazaki, N. Tokitoh, Chem. Eur. J. 2003, 9, 3530.
-
(2003)
Chem. Eur. J.
, vol.9
, pp. 3530
-
-
Takeda, N.1
Kajiwara, T.2
Suzuki, H.3
Okazaki, R.4
Tokitoh, N.5
-
18
-
-
0001198458
-
-
(Eds.: Z. Rappaport, Y. Apeloig), Wiley, New York
-
P. P. Gaspar, R. West, The Chemistry of Organic Silicon Compounds, Vol.2, Part3 (Eds.: Z. Rappaport, Y. Apeloig), Wiley, New York, 1998, p. 2463.
-
(1998)
The Chemistry of Organic Silicon Compounds
, vol.2
, Issue.PART 3
, pp. 2463
-
-
Gaspar, P.P.1
West, R.2
-
19
-
-
0000887157
-
-
a) S. Zhang, P. E. Wagenseller, R. T. Codin, J. Am. Chem. Soc. 1991, 113, 4278;
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 4278
-
-
Zhang, S.1
Wagenseller, P.E.2
Codin, R.T.3
-
20
-
-
0001099950
-
-
b) D. H. Pae, M. Xiao, M. Y. Chiang, P. P. Gaspar, J. Am. Chem. Soc. 1991, 113, 1281.
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 1281
-
-
Pae, D.H.1
Xiao, M.2
Chiang, M.Y.3
Gaspar, P.P.4
-
21
-
-
0000718569
-
-
W. Ando, K. Hagiwara, A. Sekiguchi, Organometallics 1987, 6, 2270.
-
(1987)
Organometallics
, vol.6
, pp. 2270
-
-
Ando, W.1
Hagiwara, K.2
Sekiguchi, A.3
-
22
-
-
0033592440
-
-
a) N. Sakai, T. Fukushima, S. Minakata, I. Ryu, M. Komatsu, Chem. Commun. 1999, 1857;
-
(1999)
Chem. Commun.
, pp. 1857
-
-
Sakai, N.1
Fukushima, T.2
Minakata, S.3
Ryu, I.4
Komatsu, M.5
-
24
-
-
76149141855
-
-
Two types of mechanisms have been proposed, either through a silacyclopropene intermediate by a [2+1] cycloaddition or through a zwitterionic species by a nucleophilic attack, of sila-ylide on the alkyne respectively, see: a) S. S. Sen, H. W. Roesky, D. Stern, J. Henn, D. Stalke, J. Am. Chem. Soc. 2010, 132, 1123;
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 1123
-
-
Sen, S.S.1
Roesky, H.W.2
Stern, D.3
Henn, J.4
Stalke, D.5
-
25
-
-
0000022145
-
-
b) K. Tamao, K. Nagata, M. Asahara, A. Kawachi, Y. Ito, M. Shiros, J. Am. Chem. Soc. 1995, 117, 11592.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 11592
-
-
Tamao, K.1
Nagata, K.2
Asahara, M.3
Kawachi, A.4
Ito, Y.5
Shiros, M.6
-
26
-
-
67649619341
-
-
D. Gau, T. Kato, N. Saffon-Merceron, F. P. Cossío, A. Baceiredo, J. Am. Chem. Soc. 2009, 131, 8762.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 8762
-
-
Gau, D.1
Kato, T.2
Saffon-Merceron, N.3
Cossío, F.P.4
Baceiredo, A.5
-
27
-
-
77954839987
-
-
The diastereoselectivity of the reaction was indicated by the formation of diastereomers 2 in the same proportions as those observed for the starting ylide 1 (85:15).
-
The diastereoselectivity of the reaction was indicated by the formation of diastereomers 2 in the same proportions as those observed for the starting ylide 1 (85:15).
-
-
-
-
28
-
-
0006298183
-
-
J. Belzner, H. L. Ihmels, H. Pauletto, J. Org. Chem. 1996, 61, 3315.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 3315
-
-
Belzner, J.1
Ihmels, H.L.2
Pauletto, H.3
-
29
-
-
0032578195
-
-
Only two pentacoordinate silicon-containing three-membered rings are known to date, see: a) N. W. Mitzel, U. Losehand, J. Am. Chem. Soc. 1998, 120, 7320;
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 7320
-
-
Mitzel, N.W.1
Losehand, U.2
-
31
-
-
0000024039
-
-
(Eds.: Z. Rappaport, Y. Apeloig), Wiley, New York
-
D. Kost, I. Kalikhman, The Chemistry of Organic Silicon Compounds, Vol. 2, Part3 (Eds.: Z. Rappaport, Y. Apeloig), Wiley, New York, 1998, p. 1339.
-
(1998)
The Chemistry of Organic Silicon Compounds
, vol.2
, Issue.PART 3
, pp. 1339
-
-
Kost, D.1
Kalikhman, I.2
-
32
-
-
77954842046
-
-
CCDC-766291 (2) and 766292 (8) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
-
-
-
-
33
-
-
0030598780
-
-
H. H. Karsch, R. Richter, E. Witt, J. Organomet. Chem. 1996, 521, 185.
-
(1996)
J. Organomet. Chem.
, vol.521
, pp. 185
-
-
Karsch, H.H.1
Richter, R.2
Witt, E.3
-
34
-
-
0010811287
-
-
W. Ando, Y. Hamada, A. Sekiguchi, Tetrahedron Lett. 1982, 23, 5323.
-
(1982)
Tetrahedron Lett.
, vol.23
, pp. 5323
-
-
Ando, W.1
Hamada, Y.2
Sekiguchi, A.3
-
35
-
-
0038626673
-
-
Revision E.01, Gaussian, Inc., Wallingford CT
-
Gaussian 03, Revision E.01, M.J. Frisch, G.W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M, Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M, A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
-
(2004)
Gaussian 03
-
-
Frisch, M.J.1
Trucks, G.W.2
Schlegel, H.B.3
Scuseria, G.E.4
Robb, M.A.5
Cheeseman, J.R.6
Montgomery Jr., J.A.7
Vreven, T.8
Kudin, K.N.9
Burant, J.C.10
Millam, J.M.11
Iyengar, S.S.12
Tomasi, J.13
Barone, V.14
Mennucci, B.15
Cossi, M.16
Scalmani, G.17
Rega, N.18
Petersson, G.A.19
Nakatsuji, H.20
Hada, M.21
Ehara, M.22
Toyota, K.23
Fukuda, R.24
Hasegawa, J.25
Ishida, M.26
Nakajima, T.27
Honda, Y.28
Kitao, O.29
Nakai, H.30
Klene, M.31
Li, X.32
Knox, J.E.33
Hratchian, H.P.34
Cross, J.B.35
Bakken, V.36
Adamo, C.37
Jaramillo, J.38
Gomperts, R.39
Stratmann, R.E.40
Yazyev, O.41
Austin, A.J.42
Cammi, R.43
Pomelli, C.44
Ochterski, J.W.45
Ayala, P.Y.46
Morokuma, K.47
Voth, G.A.48
Salvador, P.49
Dannenberg, J.J.50
Zakrzewski, V.G.51
Dapprich, S.52
Daniels, A.D.53
Strain, M.C.54
Farkas, O.55
Malick, D.K.56
Rabuck, A.D.57
Raghavachari, K.58
Foresman, J.B.59
Ortiz, J.V.60
Cui, Q.61
Baboul, A.G.62
Clifford, S.63
Cioslowski, J.64
Stefanov, B.B.65
Liu, G.66
Liashenko, A.67
Piskorz, P.68
Komaromi, I.69
Martin, R.L.70
Fox, D.J.71
Keith, T.72
Al-Laham, Ma.73
Peng, C.Y.74
Nanayakkara, A.75
Challacombe, M.76
Gill, P.M.W.77
Johnson, B.78
Chen, W.79
Wong, M.W.80
Gonzalez, C.81
Pople, J.A.82
more..
-
36
-
-
77954841652
-
-
-1). See Scheme Sl of the Supporting Information.
-
-1). See Scheme Sl of the Supporting Information.
-
-
-
-
37
-
-
77954843241
-
-
-1 (4c)).
-
-1 (4c)).
-
-
-
-
38
-
-
0035913753
-
-
The α, β-ambiphilic reactivity of phosphonium sila-ylides with acetylenes was postulated, see: A. Toshimitsu; T. Saeki, K. Tamao, J. Am. Chem. Soc. 2001, 123, 9210-9211.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 9210-9211
-
-
Toshimitsu, A.1
Saeki, T.2
Tamao, K.3
-
40
-
-
31544461484
-
-
(Ed.: P.J. Murphy), Oxford University Press, Oxford
-
b) A. D. Abell, M. K. Edmonds Organophosphorus Reagents (Ed.: P.J. Murphy), Oxford University Press, Oxford, 2004, p. 99.
-
(2004)
Organophosphorus Reagents
, pp. 99
-
-
Abell, A.D.1
Edmonds, M.K.2
-
44
-
-
0030991144
-
-
b) N. H. Morgon, A. B. Argenton, M. L. P. da Silva, J. M. Riveros, J. Am. Chem. Soc. 1997, 119, 1708;
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 1708
-
-
Morgon, N.H.1
Argenton, A.B.2
Da Silva, M.L.P.3
Riveros, J.M.4
|