Page 790 - Advanced Organic Chemistry Part B - Reactions & Synthesis

766 Scheme 8.16. Examples of the Ring-Closing Olefin Metathesis Reaction

CHAPTER 8 CH 3
Reactions Involving 1 a CH 3
Transition Metals F CH 3

CH
CH CH 3
CH 3 3 OTMS 98%
CH 3 OTMS 3
CH CH CH CH 3
2 b OH 3 3 OH 3
H
CH 3 CH 3 93%

3 c
OTBDPS OTBDPS
O O
Br F Br
O
O O O
CH 3 O CH 3 O
4 d CH
CH O CH 3 3
O CH 3 3
CH
F 3
CH 3
Ti(Oi Pr) 4 OTMS
OTMS
OPMB 53%
OPMB
5 e
O
CH 3
CH 3 O G CH O
CH 3 O O 3 O
C H O
C H O 3 7
3 7
69% 91:9 E:Z
OMPM
6 f PhCH O O OMPM
2
PhCH 2
OH
F
OH
N N
PhCH O PhCH O 78%
2
2
CO 2 CH CCl 3 CCl CH O C
2
7 g O CH 3 3 2 2
OMEM O CH 3
O OMEM
OH H O
O CH 3 HO
O CH 3
CH 3 O O O
CH 3 O O O
S S
8 h HO F HO
N N
O O
O O O O
OTBDMS OTBDMS
(Continued)