a) b) c) BrMg. Me BrMg. Me o yo Et₂0, 0 °C then H* work-up Cul (0.2 equiv) Et₂0, 0 °C then H* work-up NaOMe MeOH, reflux Robinson annulation

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions
Section30.SE: Something Extra
Problem 41AP: In light of your answer to Problem 30-40, explain why a mixture of products occurs in the following...
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1. Propose structures for the following products.
a)
b)
c)
d)
e)
f)
BrMg. .Me
BrMg Me
F
O₂N
Br
Br
+
NO₂
-Br
i
+
(1 equiv)
Ph
(1 equiv)
Ph
(2 equiv)
Et₂0, 0 °C
then H* work-up
Cul (0.2 equiv)
Et₂0, 0 °C
then H* work-up
NaOMe
MeOH, reflux
Robinson annulation
NEt3
DMF, heat
Pd(PPH3)4
NEt3, DMF, 60 °C
Pd(PPh3)4
NEt3, DMF, 100 °C
Transcribed Image Text:1. Propose structures for the following products. a) b) c) d) e) f) BrMg. .Me BrMg Me F O₂N Br Br + NO₂ -Br i + (1 equiv) Ph (1 equiv) Ph (2 equiv) Et₂0, 0 °C then H* work-up Cul (0.2 equiv) Et₂0, 0 °C then H* work-up NaOMe MeOH, reflux Robinson annulation NEt3 DMF, heat Pd(PPH3)4 NEt3, DMF, 60 °C Pd(PPh3)4 NEt3, DMF, 100 °C
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