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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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C6F5

NMe2

NMe

NMe2

50 vol.%

aq. MeOH

OMe

–C6F5CO2–

OMe

(31)

OMe

–H+

NMe2

solvent

NMe2

and

Me2N

azide

NMe2

capture

products

–H+

OMe

(31)

(32)

SiMe3

SbCl6–

H2C

CH2

Me3Si

SiMe3

(33)

(34)

(35)

# # #

Me3CCH2	SiHMe2			CH2CMe3
	Ph3C+ –B(C6F5)4		Me	Me
		toluene	Me	Me
		toluene		Si
				Si
				+

(36)

CMe3

O+

Me3C

Lewis acid

Me3C

OAc

–AcO–

(37)

+ Me3Si

OSiMe3

CMe3

Me3C

(38)

(39)

+H+

+OH

–H2O

F3C

C +

F3C

+OH2

(40)

+OH

+SbF6–

F3C

C+

COH + +CF3

CF4

M #

		CF3			CF3			CF3
		C+			C+	R		C+
Y		CH3	Y		H			CF3
Y		CH3	Y		H			CF3
	(41)			(42)			(43)

F3C			CF3		H
OTs				–OTs	OTs
	CF3CO2H		+
	CF3CO2H


(44)		(45)		(46)

HO CF3

CF3

CF3SO3H

(47)

H +

CF3SO3H

(48)

CF3

(51)

H (49)

(50)

PhNH2

–PhNH2

CF3

PhN

PhHN H

Ar				X		NO2
Ar						NO2
	+			C		NMe2
	+			C		NMe2
	N	MeO		+C	+
	N			R		Me CO2Me
X	Me			R		Me CO2Me
X	Me
	(52)		(53)		(54)
X = O, S			X = O, S; R = H, Me

$ $

$ $

Cl
Cl	Cl	I				Br–
Cl	Cl				I	Br
+
+		+
		+				+
Cl	Cl			+		+
				+


(55)		(56)	(57)			(58)

# # $

# #

R2N+

R R

NR2

R2N

N+

NR2

–

(59)

BF4

(60)

(61)

excess

RNH

NHR

H+

RNH

NHR

RNH2

NHR NHR

NHR

R = CHMe2, CMe3

(62)

(63)

	+
		R	+
		R	+
	MeO
	MeO
(64)	(65)		(66)

# # # #

				#
								#

K K

# #

–

OTf CHCl3

various

enol

–OTf

triflates

(67)

R1 = R2 = Me, X = CF3

R1 = Et, R2 = Ph, X = H

C6F6

CF3

40 °C

CF3

+CF2

(68)

(69)

HCO3–

F F

! " ! "

K K


H H					H
					H
			+ +H2		H
			+ +H2		H
+				+
+		(71)		+
(70)		(71)		(72)
OMe			OMe		OMe
CHPh2	hν		H
CHPh2					+
			CHPh2		+
	(CF3)2CHOH		CHPh2		+ Ph2CH
		+
		+
OMe			OMe		OMe
(73)		(74)

Me Me		Me Me		Me	Me		NH
	H2O		H
+			OH	+		+

				Ph	OH
Ph			Ph			Ph
(75)	(76)			(77)		(78)

H	H
H	H
+	+	N+

(79)

(80)

(81)

X = H, F, Cl, Br

# # # #

+	+			+
				+
(82)	(83)			(84)
CMe3				CMe3
	TFE			Me
Me3C		Me3C	+	Me
Me OTf			Me	OTf
Me OTf			Me
(85)			(86)	(87)


	X		H X
			H X
		+
		FSO3H/SO2ClF
		FSO3H/SO2ClF
Me	Me		Me	Me
	(88)			(89)


X = H, Br, NO2

$ $

% # &% &

# #

+D+

–H+

MeCH

CHD

(90)

1:1 DF–SbF5

+D+

H2C

CHD

H2C

CHD

ClCH2

CH2Cl

SbF5–SO2ClF

H2C

CH2

–78 °C

(91)

(92)

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