Page 630 - Advanced Organic Chemistry Part B - Reactions & Synthesis

604 Scheme 6.21. (Continued)

CHAPTER 6 17 q CH CH CH
Concerted 3 3 1) NaH, CS , 3 CH 3
Cycloadditions, 2
Unimolecular 2) CH 3 I
Rearrangements, and 3) heat
Thermal Eliminations O O 60%
OH

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Problems

(References for these problems will be found on page 1280.)

6.1. Predict the products of the following reactions on the basis of the reaction
mechanism and anticipated transition structure. Be sure to consider all elements
of stereochemistry. Unless otherwise specified, the reactants and reagents are
racemic.

(b)
(a) OAc
OSiMe 3
BF 3 , Et 2 O
CHCHO + CH 2 CHCHO C 14 H 26 O 2 Si
+ CH 2 C 11 H 18 O 3
CH 3
toluene, –10°C
CH 3
CH 2 CH 3
(d) H 2 C
(c) NHCO 2 C 2 H 5 CH
60°C
110°C
+ (E ) - CH 3 CH CHCHO C 11 H 17 NO 3 C 8 H 10
H
H
(f)
(e)
CH 3 200°C
CH 3 230°C
O C 11 H 16 O 3
C 14 H 22 O 2 CH 3
CH 3
CH 3 O H
O H CO 2 CH 3