Problem Set 3, Question 2

Initiation: N

N Δ C
N2 + 2x
C N N C
N

N N

C C
H SnBu3 + SnBu3

Can not
cyclize
Propagation:

abstraction
CH3
CH3
CH3
CH3
SnBu3
+ Br SnBu3
H3C Br
H3C

rapid vinyl
radical
isomerization
H
5-exo-trig
radical cyclization
CH3

CH3
H3C
CH3

CH3
5-exo-trig CH3
radical cyclization

H2C H H3C H
H SnBu3
+ SnBu3
H H
abstraction
CH3 CH3

H3C H3C

CH3 CH3