Page 1179 - Advanced Organic Chemistry Part B - Reactions & Synthesis

O 1155
(c) Ph
H O 2 CPh PROBLEMS
O
NaOCH 3 CH CO CH 3
2
2
CH 3 H
(d) THPO(CH ) CH 3 1) H O , OH THPO(CH ) H CH 3
–
2 3
H 2 2 2 3
O
CH 2) H +
3
O
H
O
(e) R R
O ,
2
OCH 3 hν, sens OCH 3
H O
O
(f) OH dicyclohexyl- OH
CH 3 O carbodiimide CH 3 CH SCH 3
2
+ CH SCH 3 H PO
3
3
4
(None of the para
isomer is formed.)
(g) O CH 3 CH 3
CH CCH CH 2 1) O 3 , MeOH CH 3 O
3
2
O O
–78°C
(CH ) SiCH 2) CF CO H H
3 3
2
3
HO 2 C CH 3 O H CH 3
O
(h) O
H O 2, CH 3
CH 3
2
CH CO H CH CH(CH ) CCO H
3
2
CH 3 + 2 2 2 2
)
2
3
Sn(CH 3 3 CH CO Na
CH 3
12.8. Indicate one or more satisfactory oxidants for effecting the following trans-
formations. Each molecule poses issues of selectivity or the need to preserve
a sensitive functional group. Select oxidants that can avoid the installation of
protecting groups. In most cases, a one-pot reaction is possible, and in no case
is a sequence of more than three steps required. Explain the reason for your
choice of reagent(s).
(a) CH 3 OH O
CH O CN H CH 3 O 2 CN H
3
2
S H S H
(b) CH
CH 3
H 3 H
O
H H