-
2
-
-
0001353029
-
-
M. Ōki, K. Shionoiri, K. Otake, M. Ono, and S. Toyota, Bull. Chem. Soc. Jpn., 66, 589 (1993).
-
(1993)
Bull. Chem. Soc. Jpn.
, vol.66
, pp. 589
-
-
Oki, M.1
Shionoiri, K.2
Otake, K.3
Ono, M.4
Toyota, S.5
-
4
-
-
0346076018
-
-
M. Ōki, J. Tsukahara, Y. Sonoda, K. Moriyama, and N. Nakamura, Bull. Chem. Soc. Jpn., 61, 4303 (1988).
-
(1988)
Bull. Chem. Soc. Jpn.
, vol.61
, pp. 4303
-
-
Oki, M.1
Tsukahara, J.2
Sonoda, Y.3
Moriyama, K.4
Nakamura, N.5
-
6
-
-
85033821249
-
-
note
-
If an open cation is produced, it is rather unstable in nonpolar solvents and deprotonation takes place very rapidly. Deprotonation from the chloronium ion can be considered rather slow because the cationic charge is not adjacent to the methyl or the chloromethyl group. Indeed, chloro-olefins are not formed in addition reactions of chlorine to normal olefins, in which the cyclic chloronium ion intermediate is proposed. When there is a rapid equilibrium between the open and the ring cations, the long lifetime in polar solvents means that the open-cation has chances to go back to the cyclic one, where the reaction takes place to produce the adduct. Solvation of the open cation in polar solvents also retards deprotonation by neutralizing the positive charge on the carbon and, when the solvent molecule leaves the cationic center, the movement being required for formation of the adduct, the rapid deprotonation takes place rather than the attack of the chloride ion on the cation.
-
-
-
-
10
-
-
2742546985
-
-
S. S. Skorokhodov, S. G. Ershova, N. V. Mikhailova, and A. A. Vansheidt, Zh. Ohshch. Khim., 31, 3626 (1961); Chem. Abstr., 57, 8555f (1962).
-
(1961)
Zh. Ohshch. Khim.
, vol.31
, pp. 3626
-
-
Skorokhodov, S.S.1
Ershova, S.G.2
Mikhailova, N.V.3
Vansheidt, A.A.4
-
11
-
-
85033817190
-
-
S. S. Skorokhodov, S. G. Ershova, N. V. Mikhailova, and A. A. Vansheidt, Zh. Ohshch. Khim., 31, 3626 (1961); Chem. Abstr., 57, 8555f (1962).
-
(1962)
Chem. Abstr.
, vol.57
-
-
-
14
-
-
2742579753
-
-
J. Sicher, M. Tichy, F. Sipos, and M. Pankova, Collect. Czech. Chem. Commun., 26, 2418 (1961).
-
(1961)
Collect. Czech. Chem. Commun.
, vol.26
, pp. 2418
-
-
Sicher, J.1
Tichy, M.2
Sipos, F.3
Pankova, M.4
-
16
-
-
0242352758
-
-
H. E. Heine, Angew. Chem., 74, 772 (1962); Angew. Chem., Int. Ed. Engl., 1, 528 (1962).
-
(1962)
Angew. Chem.
, vol.74
, pp. 772
-
-
Heine, H.E.1
-
17
-
-
84995196424
-
-
H. E. Heine, Angew. Chem., 74, 772 (1962); Angew. Chem., Int. Ed. Engl., 1, 528 (1962).
-
(1962)
Angew. Chem., Int. Ed. Engl.
, vol.1
, pp. 528
-
-
-
19
-
-
0001677656
-
-
T. A. Folgia, L. M. Gregory, and G. Maerker, J. Org. Chem., 35, 3779 (1970).
-
(1970)
J. Org. Chem.
, vol.35
, pp. 3779
-
-
Folgia, T.A.1
Gregory, L.M.2
Maerker, G.3
-
23
-
-
84981842752
-
-
P. E. Fanta, R. J. Smat, and J. R. Krikau, J. Heterocycl. Chem., 5, 419 (1968).
-
(1968)
J. Heterocycl. Chem.
, vol.5
, pp. 419
-
-
Fanta, P.E.1
Smat, R.J.2
Krikau, J.R.3
-
25
-
-
0039191566
-
-
H. W. Heine, D. C. King, and L. A. Portland, J. Org. Chem., 31, 2662 (1966).
-
(1966)
J. Org. Chem.
, vol.31
, pp. 2662
-
-
Heine, H.W.1
King, D.C.2
Portland, L.A.3
-
26
-
-
1542794793
-
-
P. G. Mente, H. W. Heine, and G. R. Scharoubin, J. Org. Chem., 33, 4547 (1968).
-
(1968)
J. Org. Chem.
, vol.33
, pp. 4547
-
-
Mente, P.G.1
Heine, H.W.2
Scharoubin, G.R.3
-
28
-
-
0014067543
-
-
A. Hassner, M. E. Loeber, and C. Heathcock, J. Org. Chem., 32, 540 (1967).
-
(1967)
J. Org. Chem.
, vol.32
, pp. 540
-
-
Hassner, A.1
Loeber, M.E.2
Heathcock, C.3
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