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Лучший способ избавиться от искушения – поддаться ему Оскар Уайльд PowerPoint PPT Presentation


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Лучший способ избавиться от искушения – поддаться ему Оскар Уайльд. Реакции ароматического нуклеофильного замещения. Реакции S N Ar. Ar-B + C -  ArC + B -. Ароматические соединения.

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Лучший способ избавиться от искушения – поддаться ему Оскар Уайльд

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S n ar

SNAr

Ar-B + C- ArC + B-


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  • , , , , .


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  • 1) , - - ;

  • 2) , ;

  • 3) , ;

  • 4) ,


S n ar1

SNAr

  • - :

    Hal-, RO-, NO2- ., .

  • , .


S n ar2

SNAr ( )


S n ar3

SNAr

  • ( - -), ,-, ( -), N-


S n ar4

SNAr

- -- ( ).


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1902 . ,


S n ar x cl br i soph so 2 ph k max k min 5

SNAr X = Cl, Br, I, SOPh, SO2Phkmax/kmin=5


S n ar f no 2 ots soph cl br i n 3 oar or sr so 2 r nh 2

SNAr F, NO2, OTs, SOPh, Cl, Br, I, N3, OAr, OR, SR, SO2R, NH2


Sb ga specific base general acid

SB-GA (Specific Base - General Acid)

  • : -

    ( )


S n ar5

SNAr


S n ar6

SNAr


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  • 1953 :


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  • , - .

  • 1973 . 80 ( )


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  • ( -)


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S r n 1

SRN1

1970 .


S r n 1 2 1 1 46

SRN12:1 = 1.46


S r n 11

SRN1

  • 2:1 = 0.63 2:1 = 5.9

    2:1 = 1.5


S r n 12

SRN1

ArX + e [ArX]-.

[ArX]-. Ar. + X-

Ar. + Y- [ArY]-.

ArX + [ArY]-. [ArX]-. + ArY


S r n 13

SRN1


S r n 14

SRN1

  • :

    PhOH PhNH2


S n 1ar

SN1Ar

ArN2+ N2 + Ar+ ()

Ar+ + Nu- Ar-Nu

Ph+ + H2OPhOH2+

PhOH2+ PhOH + H+


S n 1ar1

SN1Ar

Ar+ + CH3OHAr-OCH3 + H+

Ar+ + I- ArI

Ar+ +CN-ArCN


S n 1ar2

SN1Ar

  • 1) [Nu]

  • 2)

  • 3) Ar15N+N ArN+N15


S n anrorc

SN(ANRORC)

  • -- 70- .

  • c - ,

    , .


S n anrorc1

SN(ANRORC)


S n anrorc2

SN(ANRORC)


S n anrorc 83

SN(ANRORC)(83% )


S n anrorc3

SN(ANRORC)


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S n ar7

SNAr


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ArI + Cu ArCu

ArCu + ArI ArAr


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-


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Ar-I + Cu ArCu

ArCu + Ar-I Ar-Ar


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-


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