Page 1000 - Advanced Organic Chemistry Part B - Reactions & Synthesis

976 Scheme 10.18. (Continued)

CHAPTER 10 j CH OCH
10 O OCH 2 3
3
3
Reactions Involving SPh Bu SnH O
Carbocations, Carbenes, AIBN 88%
and Radicals as Reactive N O N
Intermediates CH 3
CH 3 O C O CH 3 CH 2 CO C H
2
2 2 5
11 k H
Bu SnH
3
CH OCH SePh O
2
2
AIBN
H 80%
12 l PhSe t-C 4 9 2
H O C
Bu SnH N
3
N Ph
H O C AIBN
t-C 4 9 2
H
C 6 5
76%
O
13 m O
Bu SnH, 1.1 equiv N
3
NCH CCO CH 3 CO CH
2
2
AIBN 2 3
CH 2 68%
CH 2 SePh
14 n CH 3 (C 2 5 3 O
H ) B
CH O C SePh
2
3
O [(CH ) Si] SiH
3 3
3
O CH 3 O CH CO CH 3
2
2
O
15 o 94% yield, 5.7:1 cis:trans
(CH ) CSePh
2 3
Bu SnH, 1.2 equiv
3
AIBN
H
O
82% 62:38 trans:cis
16 p
O H H
CH OSiR Bu SnH CH 3 CH 2 OSiR 3
3
PhSeCO 3 CH 2 3
AIBN O
H 73%
O
17 q
HO
C CPh Ph SnH, 15 equiv OH
3
CH CHCN CHPh
2
AIBN
SePh CN
C. Oxidative cyclization with Mn(O CCH )
3 3
2
18 r Mn(O CCH ) , O
2
3 3
O 2 equiv
CH 2 CH CH 2
CCH ) ,
Cu(O 2 3 2
1 equiv 51%
80°C
(continued)