Page 1015 - Advanced Organic Chemistry Part A - Structure and Mechanisms, 5th ed (2007) - Carey _ Sundberg

Table 11.3. (Continued) 999

SECTION 11.2
4 –1
38 . . 2.8 x 10 s dd Characteristics of
. E = 8.3 kcal/mol
a
Reactions Involving
Radical Intermediates
.
8 –1
39 4.2 x 10 s ee
O O 5 –1
1.4 x 10 s
ff
7 –1
40 O C . O . 9.1 x 10 s
H E = 6.8 kcal/mol
a
. . 2.5 x 10 s
5 –1
41 O C O E = 5.4 kcal/mol gg
H a
D. Other Reactions
9
–1 –1
42 (CH ) C . + O 2 (CH ) C O O . 4.9 x 10 M s gg
3 3
3 3
9
–1 –1
43 PhCH 2 . + O 2 PhCH 2 O O . 2.4 x 10 M s k
O
5 –1
44 4-CH OC H C 4 – CH )C H . 4 x 10 s hh
3
6 4
6 4
3
O . 10.2 kcal/mol
5 –1
45 (CH ) CC . O (CH ) C . + C O 3.0 x 10 s ii
3 3
3 3
7 –1
46 PhCH C . O PhCH 2 . + C O 5.2 x 10 s jj
2
E = 7.2 kcal/mol
a
CH3 5 –1
. CH 3 + C O 5.2 x 10 s aa
47
C O E = 10.0 kcal/mol
. a
CH 3 O CH3
7 –1
48 Ph C. Ph . +C O 11 x 10 s kk
CH3
CH 3
O
5 –1
49 PhC(CH ) O . PhCCH 3 +CH 3 . 7 x 10 s ll
3 2
–1 –1
6
50 Ph . + CCl 4 PhCl + . CCl 3 2.3 x 10 M s kk
. . 8 –1 –1
51 CH (CH ) + BrCCl 3 CH (CH ) Br + CCl3 2.6 x 10 M s (80° C) mm
3
3
2 3
2 3
–1 –1
9
52 Ph . + BrCCl 3 PhBr + . CCl 3 1.6 x 10 M s nn
53 CH 2 CHCH 2 . + ClOC(CH ) CH 2 CHCH Cl + (CH ) CO . nn
2
3 3
3 3
9
–1 –1
2.6 x 10 M s
54 C H . + PhSeCH CO C H C H SePh + . CH CO C H oo
2
2
2 2 5
2 2 5
8 19
8 19
–1 –1
5
1.0 x 10 M s
.
55 C H + PhSeC(CO C H ) C H SePh + CH C(CO C H ) oo
2 2 5 2
2 2 5 2
8 19
8 19
3 .
5
–1 –1
CH 3 8 x 10 M s
a. Unless otherwise noted, the rates are for temperatures near 25 C. The reference should be consulted for precise

temperature and other conditions.
b. J. Scaiano and L. C. Stewart, J. Am. Chem. Soc., 105, 3609 (1983).
c. A. Baignee, J. A. Howard, J. C. Scaiano, and L. C. Stewart, J. Am. Chem. Soc., 105, 6120 (1983).
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e. C. Chatgilialoglu, K. U. Ingold, and J. C. Scaiano, J. Am. Chem. Soc., 103, 7739 (1981).
f. S. J. Garden, D. V. Avila, A. L. J. Beckwith, V. W. Bowry, K. U. Ingold, and J. Lusztyk, J. Org. Chem. 61, 805 (1996).
g. D. V. Avila, K. U. Ingold, J. Lustyk, W. R. Dolbier, Jr., H.-Q. Pan and M. Muir, J. Am. Chem. Soc., 116, 99 (1994).
h. J. A. Franz, N. K. Suleman, and M. S. Alnajjar, J. Org. Chem., 51, 19 (1986).
i. M. Newcomb, A. G. Glenn, and M. B. Manek, J. Org. Chem., 54, 4603 (1989).