4291 Table 11. Products from Acetolysis of Substituted rhreo-3-Phenyl-2-butyl Brosylates Substituent p-Methoxya Hydrogen* Hydr0gend.P p-Chlorod m-Chlorod m-Trifluoromethyld p-Nitr0e.C
-
Olefin
Product, Zt-Acetate
50 75 50 75 75 100
0.3 351 52.6 52.1 48 72
0 0 0.1 0 1 2
99.7
100 100
76 681
3
TemD.
"c
sec-Acetate
Acetate configuration, % threo erythro
47.3 47.9 51 26
100 96 96 97 86 57
0 4 4 3 14 43
21 131
30 7
70 93
531
Reference 5a. * D. J. Cram, J . Am. Chem. Soc., 71,3863 (1949); 74, 2129 (1952). c Tosylate. d Present study. Each run was 0.05 M in the substrate and 0.053 M in sodium acetate. e Reference 6. f Isolated yields. Other yields by glpc. P S . Sivaram's data. Q
stituent constants, IS+ l 3 (Figure 2). This result indicates that in this system considerable charge is delocalized in the transition state into the phenyl ring and its activated derivatives. Evidently the geometrical situation is more favorable for such interaction in this system than in the corresponding trans-2-arylcyclopentyl derivati~es.'~Data for the products of solvolysis are summarized in Table 11.
-4.0
1
y
o
QX H,C-CH-FH-CH;
-5.0
-6.0
J
S. Winstein and B. I
