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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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$ $

M #

	TCNE
	CH2Cl2	NC		CN
	CH2Cl2	NC
		NC
		NC		CN
				CN
(10)			(11)
	SCHEME 5

$ $ ! " ! "$ $

160 °C, 22 h

C6H6, 1 bar

(12)

(13)

24%

(14) 3%

(15) 4%

(16)

(17)

(18)

SCHEME 6

H Ph

Ph2C

But

C6H5Me, ∆, 2 h

ButO2C

(19)

(20)

SCHEME 7

# K

–

Ph3P

(21)

Ph3P+

+PPh3

C6H5Me

C–

– C

(22)

(23)

86%

				R1
		N
					R2
						Ph
	N		C		C


						Ph
	(24)
R1	R2
H	CH(Me)2
H	(E)-CH					CHPh


H	3-furyl
H	4-MeOC6H4
H	4-O2NC6H4
Me	4-O2NC6H4

SCHEME 8

C6H5Me		N	R1
			R2

rt, 1 h
		N	Ph

			Ph

	(25)

SCHEME 9

J #

OPiv

hν

(26)

(27) 70%

SCHEME 10

Ph3P

CHMe

C6H5Me, –78 °C

–

PPh3

O PPh3

CHO

(28)

(29)

(30)

R = CH2OC6H4Br-p

PPh3

Br–

(32)

(31)

SCHEME 11


	MeO2C
				MeO2C
			Pd2(dba)3 (2–10 mol%)
		O	P(OPri)3 (2 equiv. to Pd)			O
H		O	toluene, reflux, 1.5–2 h			R2
			toluene, reflux, 1.5–2 h
	H	R2		H	R1
	H	R1		H	R1
	H			H
	(33)			(34)
	R1	R2
	C6H11	H
	H	C6H11
	C7H15	H
	H	C7H15

(CH2)5

SCHEME 12

N–

Cl3C

N+

Cl3C

CHNHCO2Et

EtO

CCl3

CHNHCO2Et

CO2R′

CO2Et

R′O2C

(35)

(36)

(37)

R′

CO2Me

CO2Et

SCHEME 13

CO2Me

–O

MeCO

CO2Me

(38)

CO2Me

MeO2C

(39)

3 : 2

(40)

SCHEME 14

Me	CO2Et			O		Me	CO2Et
Me						Me

H		+ O–			C6H6	H		O
	N				C6H6		N	O
TBDMS			+	NPh		TBDMS			O
TBDMS			+	NPh	70 °C, 4 h	TBDMS			O
O						O
TBDMSO				O		TBDMSO	H		NPh
TBDMSO				O		TBDMSO	H
								O
	(41)						(42)	89%
	(41)						(42)	>99% ee
								>99% ee

SCHEME 15

R1R2N H Me

R1R2N H

N O

R1R2N H

N O

O–

O O

CF3

toluene, 90 °C

(43)

(44)

(45)

SCHEME 16

CHR1CH2COR2

NOH

N+

O–

R1HC

CHCOR2

(46)

MeO2C

(47)

CH2

CHCO2Me

MeO2C

CHR1CH2COR2

(49)

(48)

SCHEME 17


	O		MeNHOH.HCl/C6H5N	O
			MeNHOH.HCl/C6H5N
			CH2Cl2
	O			O
	O	O	rt then 45–65 °C	O	O
		O	rt then 45–65 °C		O
BzO	O			BzO N+
BzO				–O Me
				–O Me
				(50)

	O–
	OH			O
	O	+
	O	NH2	O	O	O
	NH


HO	NH		BzO N
HO	HO		BzO N
	OH			Me
(52)	(–)-tetrodotoxin			(51)	79%

SCHEME 18

PhSe

			SePh				H
			SePh
N		PhSeBr			N-methylmaleimide		N
N	OH			Br–		H	O

			N+		base
		MeCN	N+		base	H
		25 °C, 1 h		OH	MeCN	O	H
(53)			(54)		25 °C, 5 h	N	O
						N
						Me
						Me
						(55)	67%

SCHEME 19

H Me

–

N+

Me +

O–

Me H

(57)

(56)

SCHEME 20

C6H5Me

SPh

N+ 110 °C, 8 h

OMe

O–

O H

OMe

O H

OMe

MeO OMe

(58)

(59)

(60)

(61)

SCHEME 21

J J

C6H4R-p

C6H4R2-p

NC6H4R-p

Na2CO3, CH2Cl2

34–48 h

–O

(62)

(63)

(64)

SCHEME 22

O–

CHCl3

80–100 °C

(67)

(65)

(66)

83%

SCHEME 23

O			H O
O			N
NH	+	H2O
NH	+	CNO	O
		296 K, 16 h	O

(68)

(69)

SCHEME 24

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