Organic Reaction Mechanisms 1997

M

J

TMS

O

Bu3SnH, AIBN

TMS

O

O

O

Br

(22)

(23)

SCHEME 8

n

n

n

O O

Bu3SnH, AIBN

O

O

+

O

O

Br

H

CO2Me

CO2Me

CO2Me

n = 1

0

:

100

n = 2

97

:

3

SCHEME 9

OBn				OBn				OBn
				SnBu3				SnBu3
N				N				N
	Bu3Sn
(24)	(25)
			SCHEME 10

M

! " K

! " ! "

K

J

! "

! "

! "

K

							Ph	Me Ph
Bu					Bu	Me
								N
N					N	N	Ph
									Ph
(26)							(27)	(28)
	SCHEME 11

J

M M

M

$

OSiPh2But

O

Et3B

O

O

Ph3SnH

(29)

OSiPh2But

OSiPh2But

O

O

O

O

Ph3Sn

O

O

+

H

Ph3Sn

(31)

(30)

SCHEME 12

O

OSnBu3

Ph

Ph

fragmentation

Bu3Sn

1,5-H transfer

O

O

(33)

(34)

SCHEME 13

OSiPh2But

O

OO +

(32)

OSnBu3

Ph

O

Me

O

Ph

O

Me (35)

M

J

Me

Me

O O

O

O

Me

PhS

Me

Me

Me

Ph

O

O

O

Me O

(36)

(37)

SCHEME 14

CN

Ph

O

Ph

S

(38)

O

S

Ph

O

Ph

O

+

+

NC

Ar

SMe

ArS

CN

(39)

(41)

(40)

SCHEME 15

J

CO2Me

ONO

+

CO2Me

OH

(42)

(43)

SCHEME 16

CO2Me

RSSR, 0.15 M, hν

H

CO2Me

H

H

H

H

HH

(44)

CO2Me

RS

+

(45)

SCHEME 17

K

! " ! "

! "

M

M

K

K

OH

O

N

O

(47)

OH

					O
						N
						O
									de 84%
		SCHEME 18
	Me	Me			Me				Me
MeO	CH2	N		N		CH2			OMe
	Me	CN			CN				Me
		(48)

M

J

J

Me	SNO		SNO
					Me	O–
Me
AcHN	CO2H	AcHN	CO2H	Ph	ONEt2	N
						+
(49)			(50)		(51)	(52)

M

MeO

	N	CPh3
(53)	(54)

K

M

J

K

K

K

K

K

K

K

M

K

Me CO2R		Me CO2R
	heat
	(ButO)2
(55)	(56)
		SCHEME 19

	CO
–	2
–toluene
–
Me

R

CO2R

(57)

M M

M

M

$

M

M

M

J

R

R

R

PhO2S

I

PhO2S

I

PhO2S

I

+

R = Me 82 : 18

R = Hex 80 : 20

SCHEME 20

R

R

O2

H

O2

H

S

R

S

R

SO2H

CH2 R

SiMe3

R

SiMe3

Si

Me

Me

(58)

(59)

SCHEME 21

SO2R

O

O

S

Si(TMS)3

Si

Si

Si(TMS)3

Me

Me

Me

Me

(60)

SCHEME 22

K

M