Page 818 - Advanced Organic Chemistry Part B - Reactions & Synthesis

794 Scheme 9.2. Homologation of Boranes by -Halocarbonyl and Related
Compounds
CHAPTER 9
Carbon-Carbon 1 a – OC(Me) 3
Bond-Forming Reactions 9 – BBN + BrCH 2 CO 2 C 2 H 5 CH 2 CO 2 C 2 H 5
of Compounds of Boron,
Silicon, and Tin 62%
2 a – OC(Me) 3
9 – BBN + Cl CHCO C H CHCO C H
2 2 5
2 2 5
2
Cl 90%
3 b t-Bu
– O
t-Bu
) CHCH CHCO C H
9-BBN CH CH(CH ) + Br CHCO C H (CH 3 2 2 2 2 5
2 2 5
2
3 2
2
Br 81%
4 c O – O
OC(Me) 3
9 – BBN CH CH CH CH 3 + CCH Br C(CH ) CH 3
2
2
2
2
2 4
80%
5 d t-Bu
O – O O
t-Bu
9 – BBN + BrCH 2 CCH 3 CH CCH 3
2
73%
6 b t-Bu
– O
t-Bu
9 – BBN CH CH CH 3 + ClCH CN CH CH CH CH CN
2
2
2
3
2
2
2
76%
7 e CH 3 O CH 3 O
CH 3 CH 2 CH 3 B + N 2 CHCCH 3 CH CH CHCH CCH 3
2
2
3
36%
2 2 5
2 6
2 2 5
2
2 5 3
8 f [CH (CH ) ] B + N CHCO C H CH (CH ) CO C H
3
3
83%
9 g BCl 2 +N CHCO C H CH CO C H
2 2 5
2 2 5
2
2
71%
10 h O O
1) LDA
(n-C H ) B + BrCH CN(C H ) (CH (CH ) CN(C H )
3
2 5
6 13 3
2 5 2
2
2 5 2
2) H 2 O 2
94%
a. H. C. Brown and M. M. Rogic, J. Am. Chem. Soc., 91, 2146 (1969).
b. H. C. Brown, H. Nambu, and M. M. Rogic, J. Am. Chem. Soc., 91, 6855 (1969).
c. H. C. Brown, M. M. Rogic, H. Nambu, and M. W. Rathke, J. Am. Chem. Soc., 91, 2147 (1969).
d. H. C. Brown, H. Nambu, and M. M. Rogic, J. Am. Chem. Soc., 91, 6853 (1969).
e. J. Hooz and S. Linke, J. Am. Chem. Soc., 90, 5936 (1968).
f. J. Hooz and S. Linke, J. Am. Chem. Soc., 90, 6891 (1968).
g. J. Hooz, J. N. Bridson, J. G. Caldaza, H. C. Brown, M. M. Midland, and A. B. Levy, J. Org. Chem., 38,
2574 (1973).
h. N.-S. Li, M.-Z. Deng, and Y.-Z. Huang, J. Org. Chem., 58, 6118 (1993).