-
5
-
-
0010421423
-
Structure and Reactivity in Aqueous Solution
-
b) "Structure and Reactivity in Aqueous Solution", R. Breslow, ACS Symp. Ser. 1994, 568, 291.
-
(1994)
ACS Symp. Ser.
, vol.568
, pp. 291
-
-
Breslow, R.1
-
7
-
-
0000749443
-
-
H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056;
-
(2001)
Angew. Chem.
, vol.113
, pp. 2056
-
-
Kolb, H.C.1
Finn, M.G.2
Sharpless, K.B.3
-
13
-
-
0141917879
-
-
NIST Standard Reference Database Number 69, March 2003, National Institute of Standards and Technology, Gaithersburg MD, 20899
-
-3 K, water has an unusually high heat capacity for a liquid; see: NIST Chemistry WebBook (Eds.: P. J. Linstrom, W. G. Mallard), NIST Standard Reference Database Number 69, March 2003, National Institute of Standards and Technology, Gaithersburg MD, 20899 (http://webbook.nist.gov).
-
NIST Chemistry WebBook
-
-
Linstrom, P.J.1
Mallard, W.G.2
-
14
-
-
0012610569
-
-
N. Rieber J. Alberts, J. A. Lipsky, D. M. Lemal, J. Am. Chem. Soc. 1969, 91, 5668.
-
(1969)
J. Am. Chem. Soc.
, vol.91
, pp. 5668
-
-
Rieber, N.1
Alberts, J.2
Lipsky, J.A.3
Lemal, D.M.4
-
15
-
-
20344390892
-
-
(BASF AG), DE 2615878, 1977
-
R. Platz, W. Fuchs, N. Rieber, U.-R. Samuel, J. Jung (BASF AG), DE 2615878, 1977 [Chem. Abstr. 1978, 88, 37 803].
-
(1978)
Chem. Abstr.
, vol.88
, pp. 37803
-
-
Platz, R.1
Fuchs, W.2
Rieber, N.3
Samuel, U.-R.4
Jung, J.5
-
16
-
-
20344376081
-
-
note
-
The amount of water used can be chosen to best balance/control the exothermicity of the reaction, as the resulting increase in total reaction volume does not constitute dilution of the reaction zone.
-
-
-
-
17
-
-
0344980985
-
-
For an example of solvent effect on the cycloaddition of quadricyclane with azodicarbonyl compounds, see: M. E. Landis, J. C. Mitchell, J. Org. Chem. 1979, 44, 2288.
-
(1979)
J. Org. Chem.
, vol.44
, pp. 2288
-
-
Landis, M.E.1
Mitchell, J.C.2
-
19
-
-
20344402204
-
-
For the only reported example, to our knowledge, of the accelerating influence of water on the reactions of azodicarboxylates, see: L. E. Gast, E. W. Bell, H. M. Teeter, J. Am. Oil Chem. Soc. 1956, 33, 278.
-
(1956)
J. Am. Oil Chem. Soc.
, vol.33
, pp. 278
-
-
Gast, L.E.1
Bell, E.W.2
Teeter, H.M.3
-
20
-
-
0001388660
-
-
Y. Leblanc, R. Zamboni, M. A. Bernstein, J. Org. Chem. 1991, 56, 1971;
-
(1991)
J. Org. Chem.
, vol.56
, pp. 1971
-
-
Leblanc, Y.1
Zamboni, R.2
Bernstein, M.A.3
-
21
-
-
33751386424
-
-
For Lewis acid mediated ene reactions of azodicarboxylates at -60°C, see: M. A. Brimble, C. H. Heathcock, J. Org. Chem. 1993, 58, 5261.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 5261
-
-
Brimble, M.A.1
Heathcock, C.H.2
-
23
-
-
1542495104
-
-
US 2262002, 1939
-
H. Hopff, C. W. Rautenstrauch, US 2262002, 1939 [Chem. Abstr. 1942, 36, 10 469].
-
(1942)
Chem. Abstr.
, vol.36
, pp. 10469
-
-
Hopff, H.1
Rautenstrauch, C.W.2
-
25
-
-
0001300546
-
-
R. Breslow, U. Maitra, D. Rideout, Tetrahedron Lett. 1983, 24, 1901.
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 1901
-
-
Breslow, R.1
Maitra, U.2
Rideout, D.3
-
26
-
-
0041818406
-
-
For an excellent recent review of the role of hydrophobic effects on reactivity, see: S. Otto, J. B. F. N. Engberts, Org. Biomol. Chem. 2003, 1, 2809.
-
(2003)
Org. Biomol. Chem.
, vol.1
, pp. 2809
-
-
Otto, S.1
Engberts, J.B.F.N.2
-
27
-
-
0000619653
-
-
P. A. Grieco, P. Garner, Z. He, Tetrahedron Lett. 1983, 24, 1897.
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 1897
-
-
Grieco, P.A.1
Garner, P.2
He, Z.3
-
28
-
-
33845551929
-
-
P. A. Grieco, K. Yoshida, P. Garner, J. Org. Chem. 1983, 48, 3137;
-
(1983)
J. Org. Chem.
, vol.48
, pp. 3137
-
-
Grieco, P.A.1
Yoshida, K.2
Garner, P.3
-
29
-
-
0000659379
-
-
and Ref. [28b]
-
However, see: R. Breslow, U. Maitra, Tetrahedron Lett. 1984, 25, 1239, and Ref. [28b].
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 1239
-
-
Breslow, R.1
Maitra, U.2
-
30
-
-
20344390169
-
-
note
-
As both starting materials and the product are oils, the neat reaction is not prone to physical "mixing" issues, which can arise when one of the reactants is a solid. Even when mixing is not an issue, we have encountered a few cases where the reactions "on water" are two- to threefold faster than the corresponding neat reaction, although the example shown here is typical.
-
-
-
-
33
-
-
0001193489
-
-
b) R. M. Coates, B. D. Rogers, S. J. Hobbs, D. R. Peck, D. P. Curran, J. Am. Chem. Soc. 1987, 109, 1160;
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 1160
-
-
Coates, R.M.1
Rogers, B.D.2
Hobbs, S.J.3
Peck, D.R.4
Curran, D.P.5
-
34
-
-
33845282891
-
-
c) J. J. Gajewski, J. Jurayj, D. R. Kimbrough, M. E. Gande, B. Ganem, B. K. Carpenter, J. Am. Chem. Soc. 1987, 109, 1170;
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 1170
-
-
Gajewski, J.J.1
Jurayj, J.2
Kimbrough, D.R.3
Gande, M.E.4
Ganem, B.5
Carpenter, B.K.6
-
37
-
-
0000518212
-
-
E. Brandes, P. A. Grieco, J. J. Gajewski, J. Org. Chem. 1989, 54, 515.
-
(1989)
J. Org. Chem.
, vol.54
, pp. 515
-
-
Brandes, E.1
Grieco, P.A.2
Gajewski, J.J.3
-
38
-
-
20344394027
-
-
See Ref. [25]
-
Grieco subsequently reported that the rearrangement of the same methyl ester in aqueous suspension was qualitatively comparable in rate and efficiency to that of the carboxylate salt in homogeneous solution. See Ref. [25].
-
-
-
-
39
-
-
0001667614
-
-
P. A. Grieco, E. B. Brandes, S. McCann, J. D. Clark, J. Org. Chem. 1989, 54, 5849.
-
(1989)
J. Org. Chem.
, vol.54
, pp. 5849
-
-
Grieco, P.A.1
Brandes, E.B.2
McCann, S.3
Clark, J.D.4
-
41
-
-
1542295909
-
-
b) J. An, L. Bagnell, T. Cablewski, C. R. Strauss, R. W. Trainor, J. Org. Chem. 1997, 62, 2505.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 2505
-
-
An, J.1
Bagnell, L.2
Cablewski, T.3
Strauss, C.R.4
Trainor, R.W.5
-
42
-
-
0025188104
-
-
a) G. Desimoni, G. Faita, P. P. Righetti, L. Toma, Tetrahedron 1990, 46, 7951;
-
(1990)
Tetrahedron
, vol.46
, pp. 7951
-
-
Desimoni, G.1
Faita, G.2
Righetti, P.P.3
Toma, L.4
-
44
-
-
0010421423
-
Structure and Reactivity in Aqueous Solution: Characterization of Chemical and Biological Systems
-
"Structure and Reactivity in Aqueous Solution: Characterization of Chemical and Biological Systems", J. J. Gajewski, N. L. Brichford, ACS Symp. Ser. 1994, 568, 229.
-
(1994)
ACS Symp. Ser.
, vol.568
, pp. 229
-
-
Gajewski, J.J.1
Brichford, N.L.2
-
47
-
-
0010421423
-
Structure and Reactivity in Aqueous Solution
-
b) "Structure and Reactivity in Aqueous Solution", W. Blokzijl, J. B. F. N. Engberts, ACS Symp. Ser. 1994, 568, 303.
-
(1994)
ACS Symp. Ser.
, vol.568
, pp. 303
-
-
Blokzijl, W.1
Engberts, J.B.F.N.2
-
48
-
-
0031763196
-
-
A. Meijer, S. Otto, J. B. F. N. Engberts, J. Org. Chem. 1998, 63, 8989.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 8989
-
-
Meijer, A.1
Otto, S.2
Engberts, J.B.F.N.3
-
50
-
-
33646934177
-
-
a) S. Otto, W. Blokzijl, J. B. F. N. Engberts, J. Org. Chem. 1994, 59, 5372;
-
(1994)
J. Org. Chem.
, vol.59
, pp. 5372
-
-
Otto, S.1
Blokzijl, W.2
Engberts, J.B.F.N.3
-
51
-
-
0000641247
-
-
b) G. K. van der Wel, J. W. Wijnen, J. B. F. N. Engberts, J. Org. Chem. 1996, 61, 9001.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 9001
-
-
Van Der Wel, G.K.1
Wijnen, J.W.2
Engberts, J.B.F.N.3
-
52
-
-
0037158732
-
-
J. Chandrasekhar, S. Shariffskul, W. L. Jorgensen, J. Phys. Chem. B 2002, 106, 8078.
-
(2002)
J. Phys. Chem. B
, vol.106
, pp. 8078
-
-
Chandrasekhar, J.1
Shariffskul, S.2
Jorgensen, W.L.3
-
54
-
-
0035954958
-
-
b) D. N. Shin, J. W. Wijnen, J. Engberts, A. Wakisaka, J. Phys. Chem. B 2001, 105, 6759;
-
(2001)
J. Phys. Chem. B
, vol.105
, pp. 6759
-
-
Shin, D.N.1
Wijnen, J.W.2
Engberts, J.3
Wakisaka, A.4
-
55
-
-
0037071660
-
-
c) D. N. Shin, J. W. Wijnen, J. Engberts, A. Wakisaka, J. Phys. Chem. B 2002, 106, 6014;
-
(2002)
J. Phys. Chem. B
, vol.106
, pp. 6014
-
-
Shin, D.N.1
Wijnen, J.W.2
Engberts, J.3
Wakisaka, A.4
-
56
-
-
0037133342
-
-
d) S. K. Pal, J. Peon, A. H. Zewail, Proc. Natl. Acad. Sci. USA 2002, 99, 1763;
-
(2002)
Proc. Natl. Acad. Sci. USA
, vol.99
, pp. 1763
-
-
Pal, S.K.1
Peon, J.2
Zewail, A.H.3
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