Organic Reaction Mechanisms 1997

Me

H

Me

H

Me

O

O

H–

Me

O

O

O

O

H

H

H

H

O

H

O

H

Me

Me

O

O–

O

Me

–O

Me

H

H

Me

Me

HCO

H

OOH

O

O

Me

H

Me

OH

O

(21)

H–

O

Me

H

OH

δ−

δ+

OH

Y

C

C

X

Y

C

NH

Ph

+

NH C

Ph

SO2

C C

X–

C

Ph

S

O

O

C

Ph

(28)

(29)

–HX

HX

OH

Y

OH

Y

C

HX

C

NH

C

Ph

N

C

Ph

S

C

S

C

X

O

C

O

O

C

O

Ph

Ph

(31)

(30)

R4 R3 O

Tol

4

3

S

N

2

R2

R1

(32) R1

= Bu, R2, R3 = H, R4 = D

(33) R1

= Bu, R2

= Me, R3 = H, R4 = H

BH

R2

δ−

O

R2

O

H

H

N

CH2

δ+

N+

N

R1

O

R1

N

αN = 5°

H2N

HO

(34)

(35)