-
2
-
-
0000607776
-
-
(b) Bailey, R. J.; Card, P. J.; Shechter, H. J. Am. Chem. Soc. 1983, 105, 6096.
-
(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 6096
-
-
Bailey, R.J.1
Card, P.J.2
Shechter, H.3
-
4
-
-
0000332479
-
-
(b) Wentrup, C.; Mayor, C.; Becker, J.; Lindner, H. J. Tetrahedron 1985, 41, 1601.
-
(1985)
Tetrahedron
, vol.41
, pp. 1601
-
-
Wentrup, C.1
Mayor, C.2
Becker, J.3
Lindner, H.J.4
-
5
-
-
0344362952
-
-
note
-
2a,b
-
-
-
-
6
-
-
0010072537
-
-
Yang, L. S.; Engler, T. A.; Shechter, H. J. Chem. Soc., Chem. Commun. 1983, 866.
-
(1983)
J. Chem. Soc., Chem. Commun.
, pp. 866
-
-
Yang, L.S.1
Engler, T.A.2
Shechter, H.3
-
8
-
-
84985687573
-
-
(b) For application of this chemistry, see: Jaworek, W.; Vögtle, F. Chem. Ber. 1991, 124, 347.
-
(1991)
Chem. Ber.
, vol.124
, pp. 347
-
-
Jaworek, W.1
Vögtle, F.2
-
9
-
-
0345225664
-
-
note
-
2b,5b-d
-
-
-
-
10
-
-
0345657492
-
-
note
-
2b,5c,d
-
-
-
-
12
-
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0000806709
-
-
(d) Kumar, A.; Narayanan, R.; Shechter, H. J. Org. Chem. 1998, 61, 4462.
-
(1998)
J. Org. Chem.
, vol.61
, pp. 4462
-
-
Kumar, A.1
Narayanan, R.2
Shechter, H.3
-
13
-
-
0345657490
-
-
note
-
6b These transformations as yet, however, are not usable preparatively.
-
-
-
-
15
-
-
0003668924
-
-
(c) Hayes, R. A.; Hess, T. C.; McMahon, R. J.; Chapman, O. L. J. Am. Chem. Soc. 1983, 105, 7787.
-
(1983)
J. Am. Chem. Soc.
, vol.105
, pp. 7787
-
-
Hayes, R.A.1
Hess, T.C.2
McMahon, R.J.3
Chapman, O.L.4
-
16
-
-
0344794699
-
-
note
-
7b-e Such Wittig rearrangements are retarded at low temperatures by TMEDA.
-
-
-
-
21
-
-
0344362950
-
-
note
-
7c
-
-
-
-
23
-
-
37049099420
-
-
(h) Yeh, M. K. J. Chem. Soc., Perkin Trans. 1 1981, 1652. The author found that benzyl methyl ether is deprotonated by n-BuLi/ TMEDA in hexane at -10 °C and the α-lithiobenzyl methyl ether formed is alkylated by 1-bromobutane (80% yield) and adds to nonenolizable ketones.
-
(1981)
J. Chem. Soc., Perkin Trans. 1
, pp. 1652
-
-
Yeh, M.K.1
-
24
-
-
0029150777
-
-
Azzena, U.; Demartis, S.; Fiori, M. G.; Melloni, G.; Pisano, L. Tetrahedron Lett. 1995, 36, 5641. The authors have communicated that α-lithio(aryl)methyl methyl ethers, as generated by metalation of arylmethyl methyl ethers with n-BuLi in THF at -40 °C in the absence of TMEDA, react with various electrophiles without serious complications from Wittig rearrangements.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 5641
-
-
Azzena, U.1
Demartis, S.2
Fiori, M.G.3
Melloni, G.4
Pisano, L.5
-
25
-
-
0344794698
-
-
note
-
2b In the present investigation, piptopyrolysis of 5H-(1-naphthyl)tetrazole at 600 °C/0.05-0.1 mm in a quartz tube packed with quartz chips yields naphthalene-1-carbonitrile and hydrogen cyanide essentially totally.
-
-
-
-
27
-
-
0345225660
-
-
note
-
A particular advantage of the present method is that 13 is a low-melting solid (mp 40.5-43.0 °C) and with slight heating can be conveniently admitted at low pressure into the pyrolysis equipment as a liquid or by simple distillation.
-
-
-
-
28
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0345657486
-
-
Sekiguchi, A.; Ando, W. Tetrahedron Lett. 1979, 4077. Sekiguchi, A.; Ando, W. J. Org. Chem. 1980, 45, 5286. These authors report that substituted phenyl(trimethylsilyl)methanols eliminate trimethylsilanol at ∼500 °C to give products of the phenylcarbenes generated.
-
(1979)
Tetrahedron Lett.
, pp. 4077
-
-
Sekiguchi, A.1
Ando, W.2
-
29
-
-
0001285796
-
-
Sekiguchi, A.; Ando, W. Tetrahedron Lett. 1979, 4077. Sekiguchi, A.; Ando, W. J. Org. Chem. 1980, 45, 5286. These authors report that substituted phenyl(trimethylsilyl)methanols eliminate trimethylsilanol at ∼500 °C to give products of the phenylcarbenes generated.
-
(1980)
J. Org. Chem.
, vol.45
, pp. 5286
-
-
Sekiguchi, A.1
Ando, W.2
-
30
-
-
0030978160
-
-
For recent summaries and treatments of the theory of isomerization of arylcarbenes, see: (a) Xie, Y.; Schreiner, P. R.; Schleyer, P. v. R.; Schaefer, H. F., Jr. J. Am. Chem. Soc. 1997, 119, 1370. (b) Matzinger, S.; Bally, T.; Patterson, E V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Wong, M. W.; Wentrup, C. J. Org. Chem. 1996, 51, 7022. Schreiner, P. R.; Karney, W. L.; Schleyer, P. v. R.; Borden, W. T.; Hamilton, T. P.; Schaeffer, H. F. J. Org. Chem. 1996, 61, 7030 and
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 1370
-
-
Xie, Y.1
Schreiner, P.R.2
Schleyer, P.V.R.3
Schaefer H.F., Jr.4
-
31
-
-
0029989970
-
-
For recent summaries and treatments of the theory of isomerization of arylcarbenes, see: (a) Xie, Y.; Schreiner, P. R.; Schleyer, P. v. R.; Schaefer, H. F., Jr. J. Am. Chem. Soc. 1997, 119, 1370. (b) Matzinger, S.; Bally, T.; Patterson, E V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Wong, M. W.; Wentrup, C. J. Org. Chem. 1996, 51, 7022. Schreiner, P. R.; Karney, W. L.; Schleyer, P. v. R.; Borden, W. T.; Hamilton, T. P.; Schaeffer, H. F. J. Org. Chem. 1996, 61, 7030 and
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 1535
-
-
Matzinger, S.1
Bally, T.2
Patterson, E.V.3
McMahon, R.J.4
-
32
-
-
0001697665
-
-
For recent summaries and treatments of the theory of isomerization of arylcarbenes, see: (a) Xie, Y.; Schreiner, P. R.; Schleyer, P. v. R.; Schaefer, H. F., Jr. J. Am. Chem. Soc. 1997, 119, 1370. (b) Matzinger, S.; Bally, T.; Patterson, E V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Wong, M. W.; Wentrup, C. J. Org. Chem. 1996, 51, 7022. Schreiner, P. R.; Karney, W. L.; Schleyer, P. v. R.; Borden, W. T.; Hamilton, T. P.; Schaeffer, H. F. J. Org. Chem. 1996, 61, 7030 and
-
(1996)
J. Org. Chem.
, vol.51
, pp. 7022
-
-
Wong, M.W.1
Wentrup, C.2
-
33
-
-
0000827672
-
-
For recent summaries and treatments of the theory of isomerization of arylcarbenes, see: (a) Xie, Y.; Schreiner, P. R.; Schleyer, P. v. R.; Schaefer, H. F., Jr. J. Am. Chem. Soc. 1997, 119, 1370. (b) Matzinger, S.; Bally, T.; Patterson, E V.; McMahon, R. J. J. Am. Chem. Soc. 1996, 118, 1535. Wong, M. W.; Wentrup, C. J. Org. Chem. 1996, 51, 7022. Schreiner, P. R.; Karney, W. L.; Schleyer, P. v. R.; Borden, W. T.; Hamilton, T. P.; Schaeffer, H. F. J. Org. Chem. 1996, 61, 7030 and
-
(1996)
J. Org. Chem.
, vol.61
, pp. 7030
-
-
Schreiner, P.R.1
Karney, W.L.2
Schleyer, P.V.R.3
Borden, W.T.4
Hamilton, T.P.5
Schaeffer, H.F.6
-
34
-
-
0345657483
-
-
references therein
-
(e) references therein.
-
-
-
-
35
-
-
0345225659
-
-
note
-
In other studies from this laboratory, loss of carbon atoms from arylcarbene precursors become major processes at temperatures above 650 °C.
-
-
-
-
36
-
-
0344794695
-
-
Ph.D. Dissertation, The Ohio State University, Columbus, Ohio, Dissertation Abstracts, Ann Arbor, Michigan
-
Carbon-carbon rearrangements of arylcarbenes were initially reported by (a) Vander Stouw, G. G. Ph.D. Dissertation, The Ohio State University, Columbus, Ohio, 1964; Dissertation Abstracts, Ann Arbor, Michigan, 1965. (b) Joines, R. C.; Turna, A. B.; Jones, W. J. Am. Chem. Soc. 1969, 91, 7754. (c) Crow, W. D.; Wentrup, C. Chem. Commun. 1969, 1387. (d) Schissel, P.; Kent, M. E.; McAdoo, D. J.; Hedeya, E. J. Am. Chem. Soc. 1970, 92, 2147. (e) Baron, W. J.; Jones, M., Jr.; Gaspar, P. P. J. Am. Chem. Soc. 1970, 92, 4739. (f) For excellent summaries and discussion of arylcarbene rearrangements, see: Gaspar, P. P.; Hsu, J.-P.; Chari, S.; Jones, M., Jr. Tetrahedron 1985, 41, 1479 and ref 2b.
-
(1964)
-
-
Vander Stouw, G.G.1
-
37
-
-
0001712535
-
-
Carbon-carbon rearrangements of arylcarbenes were initially reported by (a) Vander Stouw, G. G. Ph.D. Dissertation, The Ohio State University, Columbus, Ohio, 1964; Dissertation Abstracts, Ann Arbor, Michigan, 1965. (b) Joines, R. C.; Turna, A. B.; Jones, W. J. Am. Chem. Soc. 1969, 91, 7754. (c) Crow, W. D.; Wentrup, C. Chem. Commun. 1969, 1387. (d) Schissel, P.; Kent, M. E.; McAdoo, D. J.; Hedeya, E. J. Am. Chem. Soc. 1970, 92, 2147. (e) Baron, W. J.; Jones, M., Jr.; Gaspar, P. P. J. Am. Chem. Soc. 1970, 92, 4739. (f) For excellent summaries and discussion of arylcarbene rearrangements, see: Gaspar, P. P.; Hsu, J.-P.; Chari, S.; Jones, M., Jr. Tetrahedron 1985, 41, 1479 and ref 2b.
-
(1969)
J. Am. Chem. Soc.
, vol.91
, pp. 7754
-
-
Joines, R.C.1
Turna, A.B.2
Jones, W.3
-
38
-
-
37049134899
-
-
Carbon-carbon rearrangements of arylcarbenes were initially reported by (a) Vander Stouw, G. G. Ph.D. Dissertation, The Ohio State University, Columbus, Ohio, 1964; Dissertation Abstracts, Ann Arbor, Michigan, 1965. (b) Joines, R. C.; Turna, A. B.; Jones, W. J. Am. Chem. Soc. 1969, 91, 7754. (c) Crow, W. D.; Wentrup, C. Chem. Commun. 1969, 1387. (d) Schissel, P.; Kent, M. E.; McAdoo, D. J.; Hedeya, E. J. Am. Chem. Soc. 1970, 92, 2147. (e) Baron, W. J.; Jones, M., Jr.; Gaspar, P. P. J. Am. Chem. Soc. 1970, 92, 4739. (f) For excellent summaries and discussion of arylcarbene rearrangements, see: Gaspar, P. P.; Hsu, J.-P.; Chari, S.; Jones, M., Jr. Tetrahedron 1985, 41, 1479 and ref 2b.
-
(1969)
Chem. Commun.
, pp. 1387
-
-
Crow, W.D.1
Wentrup, C.2
-
39
-
-
33947297110
-
-
Carbon-carbon rearrangements of arylcarbenes were initially reported by (a) Vander Stouw, G. G. Ph.D. Dissertation, The Ohio State University, Columbus, Ohio, 1964; Dissertation Abstracts, Ann Arbor, Michigan, 1965. (b) Joines, R. C.; Turna, A. B.; Jones, W. J. Am. Chem. Soc. 1969, 91, 7754. (c) Crow, W. D.; Wentrup, C. Chem. Commun. 1969, 1387. (d) Schissel, P.; Kent, M. E.; McAdoo, D. J.; Hedeya, E. J. Am. Chem. Soc. 1970, 92, 2147. (e) Baron, W. J.; Jones, M., Jr.; Gaspar, P. P. J. Am. Chem. Soc. 1970, 92, 4739. (f) For excellent summaries and discussion of arylcarbene rearrangements, see: Gaspar, P. P.; Hsu, J.-P.; Chari, S.; Jones, M., Jr. Tetrahedron 1985, 41, 1479 and ref 2b.
-
(1970)
J. Am. Chem. Soc.
, vol.92
, pp. 2147
-
-
Schissel, P.1
Kent, M.E.2
McAdoo, D.J.3
Hedeya, E.4
-
40
-
-
0000581592
-
-
Carbon-carbon rearrangements of arylcarbenes were initially reported by (a) Vander Stouw, G. G. Ph.D. Dissertation, The Ohio State University, Columbus, Ohio, 1964; Dissertation Abstracts, Ann Arbor, Michigan, 1965. (b) Joines, R. C.; Turna, A. B.; Jones, W. J. Am. Chem. Soc. 1969, 91, 7754. (c) Crow, W. D.; Wentrup, C. Chem. Commun. 1969, 1387. (d) Schissel, P.; Kent, M. E.; McAdoo, D. J.; Hedeya, E. J. Am. Chem. Soc. 1970, 92, 2147. (e) Baron, W. J.; Jones, M., Jr.; Gaspar, P. P. J. Am. Chem. Soc. 1970, 92, 4739. (f) For excellent summaries and discussion of arylcarbene rearrangements, see: Gaspar, P. P.; Hsu, J.-P.; Chari, S.; Jones, M., Jr. Tetrahedron 1985, 41, 1479 and ref 2b.
-
(1970)
J. Am. Chem. Soc.
, vol.92
, pp. 4739
-
-
Baron, W.J.1
Jones M., Jr.2
Gaspar, P.P.3
-
41
-
-
0001190191
-
-
and ref 2b
-
Carbon-carbon rearrangements of arylcarbenes were initially reported by (a) Vander Stouw, G. G. Ph.D. Dissertation, The Ohio State University, Columbus, Ohio, 1964; Dissertation Abstracts, Ann Arbor, Michigan, 1965. (b) Joines, R. C.; Turna, A. B.; Jones, W. J. Am. Chem. Soc. 1969, 91, 7754. (c) Crow, W. D.; Wentrup, C. Chem. Commun. 1969, 1387. (d) Schissel, P.; Kent, M. E.; McAdoo, D. J.; Hedeya, E. J. Am. Chem. Soc. 1970, 92, 2147. (e) Baron, W. J.; Jones, M., Jr.; Gaspar, P. P. J. Am. Chem. Soc. 1970, 92, 4739. (f) For excellent summaries and discussion of arylcarbene rearrangements, see: Gaspar, P. P.; Hsu, J.-P.; Chari, S.; Jones, M., Jr. Tetrahedron 1985, 41, 1479 and ref 2b.
-
(1985)
Tetrahedron
, vol.41
, pp. 1479
-
-
Gaspar, P.P.1
Hsu, J.-P.2
Chari, S.3
Jones M., Jr.4
-
43
-
-
37049126375
-
-
(b) Garner, G. V.; Mobbs, D. B.; Suschitsky, H.; Millership, J. S. J. Chem. Soc. C 1971, 3693.
-
(1971)
J. Chem. Soc. C
, pp. 3693
-
-
Garner, G.V.1
Mobbs, D.B.2
Suschitsky, H.3
Millership, J.S.4
-
44
-
-
0344794692
-
-
Ph.D. Dissertation, The Ohio State University, and ref 11
-
Bailey, R. J. Ph.D. Dissertation, The Ohio State University, 1974, and ref 11.
-
(1974)
-
-
Bailey, R.J.1
-
45
-
-
0344362948
-
-
note
-
-1 mm each yield 53 and 54 in ∼7% and 1% yields; phenanthrene, 9-methylphenanthrene and 9-phenanthrenecarbonitrile are also formed.
-
-
-
-
53
-
-
0345225656
-
-
Sadtler Research Laboratories, Inc., Philadelphia, PA
-
1H NMR Spectrum 2349M. Sadtler Research Laboratories, Inc., Philadelphia, PA.
-
1H NMR Spectrum 2349M
-
-
|