Amidines in Organic Synthesis - Superbases for Organic Synthesis - page 55

O OMe

O

O

S Y HC(OMe) 3

p-TsOH H 2 O

(MeO) 3 C Br

S

S

I Bu

N

I Bu

N X

I Bu

NH 2

Y = Br
Y = N 3

X = OMe
X = NHR

RNH 2
CH 3 OH

NaN 3

1) KH, THF 2)

O

Ph 3 P

THF

S

I Bu

N OMe

O O

O

S S

S

I Bu

N N N

I Bu

I Bu

N OMe

O

O

O

R

S

S

I Bu

S

N

N
H

I Bu I Bu

N

N

K 2 CO 3

N

R = Me, i Bu, Ph, CF 3 CH 2

Synthesis of N,N 0 -disulfinyliminoamidines from N-sulfinylamine

Scheme 3.10