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Казанский национальный исследовательский технологический университет

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Химия

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Organic Reaction Mechanisms 1997

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+ –

Na CH

(9)

(10)

(12)

(11)

a; YZ =

(CO2Me2O2C)

b; Y = Z = CN

c; Y = Z = COMe

d; Y = Z = CO2Et

e; Y = (N

CPh2), Z = CO2Me

f; Y =(N

CH(p-ClC6H4), Z = CO2Et

g; Y = Ph, Z = CN

	ET
RX + Nu–				R· + X– + Nu·
RX + Nu–				R· + X– + Nu·
				–
R· + Nu–			(RNu)·
R· + Nu–			(RNu)·
–
(RNu)· + RX				RNu + R· + X–
(RNu)· + RX				RNu + R· + X–
		SCHEME 1

$ ! " ! "

! $ "

M #

–

M+

O + R

O– M+

O–

M+·

SCHEME 2

K12

K23

(13)

(14)

(15)

O O

	K12		K23
R
		OH

(16)

a; R = Me b; R = Ph c; R = H

R	R
(17)	(18)

K12

K23

(19)

(20)

(21)

K34

(22)

		O		Me	O O	Me		O
COMe					C C Me	Me		O
COMe					C C Me
	COMe			Me



(23)			(27)		(24)		(28)

COMe

(25)

(29)

	Me	O
COMe

	COMe				(30)
	(26)
OSiCl3	OSiCl3		Me
		Ph
		Ph	N		O
	Me		N		O
	Me			P
				P	N
		Ph	N
			N

			Me
(31)	(32)		(33)

! "

(34)

a; R1 = R2 = H

b; R1 = H, R2 = CO2Me

! " ! J

toluene

OLi

–

lithium

PMP

(38)

(36)

MeO

OMe

amide

(37)

(35)

favoured by

s-BuLi

3.0 kcal mol–1

O–

–O

(40a)

(40b)

(39)

MeBr

Me +

(41a)

(41b)

		Ph				Ph
					O
	Bn N		BnO	C	N
	Bn N		BnO	C	N

	N	O		N		O
	N			N
Bn			Bn
Bn			Bn
	(42)				(43)

		R
CONHBn	I2	I		I2


2,6-lutidine			O	NHBn
R			O
(44)			(45)
I		R		I



CONHBn		I		NBn
CONHBn		I
R			O
R			O
(47)			(46)
			(46)

R – O

HO2C

(Z)-(48)

–

HO2C

(E)-(50)

O– HO2C

threo-(49)

O– HO2C

erythro-(51)

But

–

CO But

CO2But

(53)

(55)

ArN

Tos

(52)

Tos

–

Tos

(54)

(56)



		$

# ! " $ $

# ! "! " ! "

# ! " ! " ! " $ $

2 CN–

–

H2C

CHCN

CH2

OCOAr2

(57)

(58)

(59)

SCHEME 3

M J

	PhO2S	n
	Me	n
	Me
Ph		Li		aggregates
				aggregates

	N	N	OLi
	Me
		(60)

			$
			$

M J

$ "

	CN			CN		S CN
						S CN
S	S	n-BuLi S	S		S
S	S	n-BuLi S	S
			–
			–
	N		N		(CH2)n		N
	N		N		(CH2)n		N
	(CH2)n=2,3		(CH2)n
			SCHEME 4

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