5) 6) 7) 8) 9) R SR R" mgar Meo Me '•N•" H HCI pyridine 요 R H J HO. R "P(OET)2 HOCO₂R CH3C(OET) 3 CH3CH₂CO₂H heat OH R' R' RN-OME Me Weinreb amide + HO₂CR + COS + RSH EtO. R'M R'M = R'Li 1) Cy-N=C=N-Cy 2) R'OH CO₂R¹ R'MgX R'₂CuLi [3,3]-Sigmatropic EtO. rearrangement OR' J₂ R R¹ R

Chemistry & Chemical Reactivity
10th Edition
ISBN:9781337399074
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Chapter23: Carbon: Not Just Another Element
Section: Chapter Questions
Problem 52PS
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Question

Propose a mechanism for the following transformation

5)
6)
7)
8)
9)
يد
R₁
RCI
i
R H
HO.
R
SR
S
MeO
+
Me
N
H HCI
pyridine
R'
+ HO₂CR
R'A + COS + RSH
OMe
Me
Weinreb amide
"P(OET)2
HⒸ CO₂R¹
CH3C(OET) 3
CH3CH₂CO₂H
heat
OH
EtO
R'M
R'M = R'Li
1) Cy-N=C=N-Cy
2) R'OH
CO₂R¹
R'MgX
R'₂CuLi
[3,3]-Sigmatropic EtO.
rearrangement
OR'
R R
R
Transcribed Image Text:5) 6) 7) 8) 9) يد R₁ RCI i R H HO. R SR S MeO + Me N H HCI pyridine R' + HO₂CR R'A + COS + RSH OMe Me Weinreb amide "P(OET)2 HⒸ CO₂R¹ CH3C(OET) 3 CH3CH₂CO₂H heat OH EtO R'M R'M = R'Li 1) Cy-N=C=N-Cy 2) R'OH CO₂R¹ R'MgX R'₂CuLi [3,3]-Sigmatropic EtO. rearrangement OR' R R R
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