Organic Reaction Mechanisms 1997

Ar

Ar

Ar

+

EtO

Ar

Ar

Ar

Ar

+ ClO4–

–2e–

+

Ar

EtO

Ar

Ar

(95)

(96)

R

R

R

Me

2+

H

H

S

R

+

O

R

R

(97)

(98)

(99)

R = H, Me

OH

H2O +

H

OH

+H+

H

–H+

H

(100)

H

H

(102)

(101)

TsO

H

EtOH–H2O

+

(103)

H

(104)

R

N

C

+

X

OBb

(105)

(106)

(107)

–196 °C

+

Me

(108)

Me

Me

(109)

Ar

Y

C

C

LG

Y′

(1)

a; LG = OTf

b; LG = OMs

Cl

H

MeS

H

Ar

H

C

C

MeS–

C

C

+

C

C

MeCN

CO2Me

Ar E

CO2Me

Ar

E

CO2Me

MeS

Z

(2)

(3)

(4)

Ar

C

C

H

Ar

C

C

CO2Me

(5)

(6)

R

H

R

H

R

OAc

AcOH

+

C

C

+

C

C

IPh+

C

C

H E

H

E

OAc

H

Z

H

(7)

BF4–

(8)

(9)

H

H

a; R = C6H5

(10)

b; R = n-C8H17