Page 1110 - Advanced Organic Chemistry Part B - Reactions & Synthesis

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5
CHAPTER 12
C
Oxidations
O
1.340
C
C 4
2 C 3

C
O -C -C -C = 117.3 degree
2
1
3
4
1

1 O
1.342
C C
2 C 3 4 C 5

C
4
3
2
O 1 -C -C -C = 120.4 degree
1

6
C
1 O
1.346
C C
3
2 C 4
C 5

C
1 O -C -C -C = 116.8 degree
2
4
3
1
Fig. 12.5. Minimum energy conformations for allylic alcohol. 3a,
3b, and 3c. Reproduced from J. Org. Chem., 67, 1427 (2002), by
permission of the American Chemical Society.