Organic Reaction Mechanisms 1997

Organic Reaction Mechanisms, 1997 An Annual Survey Covering the Literature Dated December 1996 to November 1997 Edited by A.C. Knipe and W.E. Watts Copyright © 2001 John Wiley & Sons, Ltd

ISBNs: 0-471-89935-6 (Hardback); 0-470-84580-5 (Electronic)

J

K

J

O

O

O

O

H+

OH

LDA

R

R

NEt2

R

Me

NEt2

–

CONEt2

CH2

(1)

(2)

O

RO

(3)

SCHEME 1

J

K

M

J

S

S

SLi

P(OR)2

BuLi

P(OR)2

O

Li

O

P(OR)2

O

H+

SH

P(OR)2

O

SCHEME 2

	OMe			OMe				OMe
	CHPh2				H
								+
					CHPh2
				+				+ PhCH2
	OMe				OMe			OMe
(4)				(5)

OMe		OMe
OMe		+
		OMe
CHPh2		H
		CHPh2
	(6)
		SCHEME 3

K

M

M

H

+

MeO

MeO

H

ZrCl4

MeO

H

H

(ZrCl4)2

ZrCl3

[ZrCl5]–

+

–

OMe

MeO Cl

ZrCl4

–ZrCl4. HCl

ZrCl3

SCHEME 4

–

OH

AlCl2

O

O

AlCl3

+

H2O

(7)

(8)

(9)

CArAr′OH

H+

+

CArAr′OH

Ar2(HO)C

Ar2C

(10)

(11)

Ar = 2,6-(MeO)2C6H3

Ar

CAr

C

Ar′

Ar

(12)

M

M

J

J

OH								OH
O					TFA		HO
					(R2 = H)					R
		R
O	R1
R2	R3						O	R1 R3
	(13)							(14)
Me				Me					Me

Base

HOEWG O2 –OEWG OEWG

R				R		R
(15)
O		OH		O		O
						H2C

OEWG HOEWG HOEWG

R R R

	+		+
O		O		O

OEWG OEWG –OEWG

R R R

O

OEWG

R

(16)

SCHEME 5

–OCOR3

OH

O

H

O

R1

(R3CO)2O

R1

R1

S+

S+

S+

R2

O–

R2

OCOR3

–OCOR3

(17)

R2

O

O

2

SSR

2

+

R

1

R1

R

R2S

OCOR3

O

(19)

(18)

+	+
(p-RC6H4)MeCHC(OH)C6H4R′-p		MeCHC(OH)(C6H4R′-p)(C6H4R-p)
(20)	(21)

Ar		+
TsO	CO2Me				Ar
						O
					O

O

OMe

SCHEME 6

Ph
	Ph		Ph
HO	OH	+	+ Ph
		H2O

CF3SO3H

SCHEME 7

O

O

Cl

H

R

R

+

H

			CO2H	+
R						R
									O
				SCHEME 8

Mes		OH									NMe2
Mes						Me		Me
							+	O
				NMe2					Mes
							Me
	(22)

	Me			NMe2							NMe2
Me						Me		Me
	O						+	O
		Mes							Mes
	Me						Me
	(24)							(23)

M

OH

OMe

O–

OMe

O

O

MeO

CHO

MeO

CHO

OMe

OMe

(25)

MeO

CHO

O–

H

O

O

OH

O

MeO

MeO

OMe

OMe

(27)

(26)

M

CONHR3

CONHR3

R2

I

I

aq.NaOH

R2

I

I

R1NHCO

O

CONHR3

HO

N

CONHR3

I

I

R1

(28)

(29)

R

NO

R

O–

R

N

N

+

N+

O–

NH4

(30)

(31)

K

N		Ar		N					N
R			DAIB						R
				R
NH2				–					N
				N		X
									H
(32)									(33)
				X = Cl, Me2S+, Me3N+, PhSO2O

J

K

K K

K