Page 797 - Advanced Organic Chemistry Part B - Reactions & Synthesis

PdCl , O O 773
2
(a) (6 mol %)
CH (CH ) CH CH 2 + CO + (CH CO) O CH 3 (CH 2 ) 5 CHCH 2 COCCH 3 PROBLEMS
2 5
3
3
2
, CuCl
O 2 2
3
(b) OSi(CH ) Pd(OAc) 2 CH CO 2
3 3
CHCH CH C CH O
CH 2 2 2 2 CH CN CH 3
3
10 h, 25°C
(c) CH 3 CH CH 3 CH
3 CO, H 2 H 3
O PhCH O
PhCH 2 2
Rh (OAc) ,
2
2
OH PPh , 100°C O
3
(d) OH
[RhCl(COD)] 2 CH (CH )
(0.5 mol %) 3 2 5
PhCOCl + CH (CH ) C CH Cl
3
2 5
PPh 3 (1 mol %) Ph
(e)
cat G PhCO 2 CH 2
CH C CH +
PhCO 2 2
(see 762)
8.4. Indicate appropriate conditions and reagents for effecting the following trans-
formations. Identify necessary co-reactants, reagents, and catalysts. One-pot
processes are possible in all cases.
(a) CH 3
(CH CH ) C CHCH CH Br (CH CH ) C CHCH CH C
2
2
3
2 2
2
2 2
2
3
CCO CH 3
2
(b) Br CH CHCN
H
NHCCH 3 NHCCH 3
O O
2
(c) CH 3 O C CO CH 3
2
CH 3 (CH 2 ) 3 Br + CH O CC CCO CH 3
2
2
3
2 3
CH 3 (CH ) H
(d) O O
CH
CH 3 3 CH CH CH CH 2
2
2
CH 3 CH 3
CCH
O 2 3
O CCH
(e) 2 3 (CH ) CH
3 2
(CH ) CH CH 3
3 2
CH Br
2
CH 3
CH
CH Br 3
CH 3 2