Äîêóìåíò âçÿò èç êýøà ïîèñêîâîé ìàøèíû. Àäðåñ îðèãèíàëüíîãî äîêóìåíòà : http://chem.msu.ru/rus/journals/jvho/2006-3/139.pdf Äàòà èçìåíåíèÿ: Mon Oct 2 16:27:38 2006 Äàòà èíäåêñèðîâàíèÿ: Sun Apr 10 19:24:42 2016 Êîäèðîâêà:

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EBL?J:LMJ:
1. Europian Chemical News. 13-19.10.1997. 2. www.the-innovation-group.com. Chem. Profiles. Aniline.htm. 3. Hudlicky M. Reduction in Organic Chemistry, Chichester Ellis Horwood, 1984, 309 p. 4. GbdheZ_\ XL Ydm[khg :F :gbebg. F Obfby 5.

18.

19. 20. 21.

6. 7. 8. 9.

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22. 23. 24. 25.

1975.

10. Johnstone R.A., Wilby A.H., Entwistle I.D. Chem. Rev., 1985, j -- 170. 11. BaZdh\bq WG Ob^_d_ev FE Mki_ob obfbb l \ui k --777. 12. Khdhevkdbc ><. DZlZebaZlhju ]b^jh]_gbaZpbb :efZ-:lZ GZmdZ DZaKKJ k --20. 13. >hjhoh\ <= ;Zj_edh << ;Zev`bgbfZ_\ ;K XjZgh\ B: Obf ijhf-clv k --48. 14. Qmglyg hjhoh\ <= ;hcdh ;K ;Zev`bgbfZ_\ ;K ;Zj_edh << >hde J:G l k --506. 15. ;Z[g__\ :> =hklbdbg he]h\ KG b ^j
LZpblh\ < B Ihih\ E D =hklbdbg < I Ba\ \mah\ Ob fby b obf l_ogheh]by k --47. Yd_jkhg < B =hehkfZg ? A Mki_ob obfbb l \ui k --806. DheoZmg O F Ohelhg > Lhfikhg > L\b]] F Gh\u_ imlb hj]Zgbq_kdh]h kbgl_aZ IjZdlbq_kdh_ bkihevah\Zgb_ i_j_ oh^guo f_lZeeh\ I_j k Zg]e F.: Obfby, 1989, 400 k.


26.

KeZ\bgkdZy < : Dj_ce_ > J b^j DZlZeblbq_kdb_ f_lh^u \hkklZgh\e_gby b ]b^jbjh\Zgby gbljhkh_^bg_gbc Ij_ ijbgl Bgklblml hj]Zgbq_kdh]h kbgl_aZ :G EZl\KKJ 985, k NZjjZmlh J >` O_d J F Dbg_lbdZ b dZlZeba l k --652. IZl_gl JN Dhaeh\ : B A[Zjkdbc < E =jmgkdbc < G Bevbg : K DhfZjh\ : : Obfbq_kdZy ijhfure_gghklv k_]h^gy k --18. Dhaeh\ : B A[Zjkdbc < E Bevbg : K F_jdbg : : LZf `_ k --21. Lbs_gdh K < Dhaeh\ : B ;_kiZeh\ : < =jmgkdbc < G LZf `_ k --51. Djueh\ H < =_l_jh]_gguc dZlZeba F BDP :dZ^_fdgb ]Z k Dhaeh\ : B A[Zjkdbc < E Bevbg : K F_jdbg : : K[ lj B F_g^_ e__\Z k --43. Ebl\bg ? N RZjn < A Jhk obf ` @ Jhk obf h[-\Z bf > B F_g^_e__\Z l k --98.
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27. Aniline production. Ullmann's Encyclopedia of Industrial Chemistry, Syxth Edition, 2002 Electronic Release. 28. IZl_gl ?J 29. IZl_gl KR: 30. Aniline the builder Europian Chem. News, 1-7.03.2004. 31. A[Zjkdbc
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3

iZjZ-iheh`_gbb d gbljh]jmii_ \ lh \j_fy dZd 4-aZf_s_ggu_ gbljhZj_gu ih^\_j]Zxlky bkdexqbl_ev gh hjlh-ZlZd_ >@ GZfb bkke_^h\Zehkv \aZbfh^_ckl\b_ ZjbeZp_lhgbljbeh\ k gbljh[_gaheZfb kh k\h[h^guf iZjZ-iheh-

`_gb_f \ kj_^_ kibjlZ b ijb ba[uld_ ]b^jhdkb^Z dZeby >@ < j_amevlZl_ j_Zdpbb h[jZamxlky fhghhdkbfu ZjbepbZghf_lbe_gobghgZ k \uoh^Zfb --80%, y\eyxsb_ky p_ggufb ihemijh^mdlZfb \ hj]Zgbq_kdhf kbgl_a_ ko_fZ 9).
NO
2

HO X + Ar H C
2

CN N Ar X

CN

>=D
3U2+ KOH
CN

AlkO Alk-I N

>FN/

K2CO

Ar
3

X


6

1-

gZnlbe

X= H, Cl; Ar = Ph, 2-HKG3 $ON (W >=D-Bu.

K G4

, 3,4-



HKG3)2K6G3

,

Ko_fZ



Hkh[_gghklvx ^Zgghc j_Zdpbb y\ey_lky h[jZah\Zgb_ kl_j_hbahf_jguo nhjf ? b Z ZjbepbZghf_lbe_gobghg fhghhdkbfh\ qlh [ueh ^hdZaZgh ih ki_dljZf YFJ 1G Khhlghr_gb_ nhjf ? b Z aZ\bkbl hl gZebqby aZf_klbl_ e_c \ obghb^ghf b ZjhfZlbq_kdhf y^jZo Kbgl_abjh \Zggu_ kh_^bg_gby ih^\_j]Zeb ^Zevg_cr_fm fh^bnb pbjh\Zgbx \ qZklghklb Zedbebjh\Zgbx \ mkeh\byo j_Zdpbb @ hibkZgh \aZbfh^_ckl \b_ -gbljhoehj[_gaheZ k n_gbeZp_lhgbljbehf \ f_lZ ghe_ ijb ba[uld_ ]b^jhdkb^Z dZeby ijb\h^ys__ d h[jZ ah\Zgbx -oehj-3-n_gbe-2,1-[_gabahdkZaheZ ko_fZ 10).
NO2 H2C + Cl C N KOH CH3OH Cl N O

WlZ j_Zdpby gmde_hnbevgh]h aZf_s_gby \h^hjh^Z khijh\h`^Z_lky pbdebaZpb_c k mqZklb_f gbljh]jmiiu HgZ y\ey_lky m^h[guf kihkh[hf ihemq_gby -[_gabahdkZaheh\ ZgljZgbeh\ -- fgh]hieZgh\uo kbglhgh\ lhgdh]h hj]Zgbq_kdh]h kbgl_aZ ihemijh^mdlh\ \ ijhba \h^kl\_ fhghf_jh\ b [bheh]bq_kdb Zdlb\guo \_s_kl\ ljZgd\bebaZlhjh\ fZehc ]jmiiu >ey \uykg_gby f_oZgbafZ j_Zdpbb ZjhfZlbq_kdh]h gmde_hnbevgh]h aZf_s_gby \h^hjh^Z b hij_^_e_gby \hafh`ghklb __ ijbf_g_gby \ kbgl_a_ p_ggh]h deZkkZ hj]Zgbq_kdbo \_s_kl\ -[_gabahdkZaheh\ [ueb ijh \_^_gu dbg_lbq_kdb_ bkke_^h\Zgby wlhc j_Zdpbb >-- @ Ihemq_ggu_ j_amevlZlu k\b^_l_evkl\mxl h ijhl_ dZgbb ijhp_kkZ h[jZah\Zgby -[_gabahdkZaheh\ ih ^\mf Zevl_jgZlb\guf imlyf Koh^kl\h h[hbo gZijZ\e_ gbc \ kdhjhklvhij_^_eyxs_c klZ^bb h[jZah\Zgb_ /-dhfie_dkZ \ aZ\bkbfhklb kdhjhklb hl dhgp_gljZ pbb j_Z]bjmxsbo \_s_kl\ ijbjh^u jZkl\hjbl_ey b aZf_klbl_ey \ km[kljZl_ iha\hey_l kqblZlv qlh jZaeb qby f_`^m imlyfb j_Zdpbb k\yaZgu k h[jZah\Zgb_f /-dhfie_dkh\ jZaghc kl_j_hbahf_jghc kljmdlmju GZ hkgh\Zgbb ^Zgguo dbg_lbq_kdbo bkke_^h\Zgbc b d\Zglh\hobfbq_kdh]h fh^_ebjh\Zgby gZfb k^_eZgh ij_^iheh`_gb_ h ke_^mxs_f f_oZgbaf_ j_Zdpbb f_`^m 4-gbljhoehj[_gahehf b n_gbeZp_lhgbljbehf ijhl_ dZxs_c \ kibjl_ ijb ba[uld_ ]b^jhdkb^Z gZljby Hk gh\guf klZ^byf ^Zggh]h ijhp_kkZ ij_^r_kl\mxl hq_gv [ukljh mklZgZ\eb\Z_fu_ jZ\gh\_kby k mqZklb_f ]b^jh dkb^Z gZljby
PhCH2CN + NaOH C2H5OH + NaOH PhCHCN­ + NaOH


PhCHCN­ + Na+ + H2O C2H5O­ + Na+ + H2O PhCCN2­ + Na+ + H2O


GZ ke_^mxs_c klZ^bb hij_^_eyxs_c kdhjhklv \k_]h ijhp_kkZ h[jZamxlky bahf_jgu_ /-dhfie_dku ijbq_f j_Zdpbb ijhl_dZxl k jZaebqgufb Zdlb\Zpbhggufb [Zjv_jZfb ko_fZ 11).


Cl

NC ­ CH

NC Ph HC H Cl N

O
+

­ ­

O + NO

2

Cl

H Ph CN CH O N+ O

­ ­

Ko_fZ



AZl_f hkms_kl\eyxlky [uklju_ ij_\jZs_gby /dhfie_dkh\ \ dhg_qguc ijh^mdl ko_fZ 12). Ihemq_ggu_ dbg_lbq_ db_ aZdhghf_jghklb iha\heb eb jZkijhkljZgblv bamqZ_fuc lbi \aZbfh^_ckl\bc gZ [he__ rbjhdbc jy^ gbljhkm[kljZlh\ b ZjbeZp_lhgbljb eh\ ko_fZ 13).
F > @

Ko_fZ



143


< X Hjeh\ : > Dhlh\ < < =Zg`Z : B JmkZdh\


Cl H CN H O N+ O­
­

Cl H N+ O­ CN HO

Cl

C­ CN HO

N+ OH

Cl

Cl CN­ Cl

C­ CN

N O CN O­

N

O

N

Ko_fZ
C R NO
2


N O R Ar
O

N N aO H R'OH + H2 C Ar

]^_

R = Cl, Br, I,
O

KHHG,

CONH2,

H 2C

O CH O



C H2



H 2C C H2

O C O CH3





Cl

Cl









Ar = Ph, 3-ClC6H4, 4-ClC6H4, 2-CH3C6H4, 4-CH3C6H4, 2-CH3OC6H4, 4-CH3OC6H4, 3,4-(CH3O)2C6H3, 2-CH3SC6H4, 3,4-(Cl)2C6H3, 3,4-(C2H5O)2C6H3, 1-gZnlbe, 2-lb_gbe.

Ko_fZ


3

>ey g_kbff_ljbqguo gbljhZjhfZlbq_kdbo kh_^bg_ gbc j_Zdpby gmde_hnbevgh]h aZf_s_gby \h^hjh^Z ijh l_dZ_l j_]bhki_pbnbqgh LZd ba -^boehj-4-gbljh[_gaheZ h[jZamxlky ZgljZgbeu bkdexqbl_evgh ebg_c gh]h kljh_gby ^Zggu_ ki_dljhkdhibb YFJ 1G ko_ fZ 14).


X O N
+

O + HC 2 Ar

C

N NaOH ROH

O­ X O Ar
H2C O C O CH3

Cl Cl

NO 2 CN + H2C Ar

Cl NaOH ROH Cl

N O Ar
]^_

N O

Ar = Ph, 4-ClC6H4, 2-CH3OC6H4, 4-CH3OC6H4, 3,4-(CH3O)2C6H3, 3,4-(C2H5O)2C6H3.

]^_

X = H,

C H2

Ko_fZ


4


Ar = Ph, 4-ClC6H4, 2-CH3OC6H4, 3,4-(CH3O)2C6H3, 3,4-(C2H5O)2C6H3, 1-gZnlbe

< lh `_ \j_fy \aZbfh^_ckl\b_ -gbljh^b[_gahnmjZgZ b _]h -aZf_s_ggh]h ijhba\h^gh]h k ZjbeZp_lh gbljbeZfb ijb\h^bl d -[_gabahdkZaheZf Zg]meyjgh]h kljh_gby ^Zggu_ YFJ 1G ki_dljhkdhibb >Zgguc ih^oh^ ^_eZ_l \hafh`guf ihemq_gb_ dhg^_gkbjh\Zg guo ZjhfZlbq_kdbo kbkl_f kh^_j`Zsbo g_kdhevdh ]_l_jhpbdebq_kdbo njZ]f_glh\ ko_fZ 15). KhihklZ\e_gb_ wdki_jbf_glZevguo ^Zgguo b j_amev lZlh\ d\Zglh\hobfbq_kdbo jZkq_lh\ \ jZfdZo ihemwf ibjbq_kdh]h f_lh^Z :F iha\hey_l h[tykgblv ^Zggmx
>@  

Ko_fZ


5


j_]bhki_pbnbqghklv kljmdlmjhc gbar_c k\h[h^ghc fhe_dmeyjghc hj[blZeb GKFH km[kljZlZ \ jZfdZo fh^_eb hj[blZevguo \aZbfh^_ckl\bc b bkdexqblv aZjy ^h\uc nZdlhj ba qbkeZ kms_kl\_ggh \ebyxsbo gZ gZ ijZ\e_gb_ gmde_hnbevghc ZlZdb Kbff_ljbqgu_ iheby^_jgu_ iZjZ-aZf_s_ggu_ ^b gbljhZj_gu j_Z]bjmxl k ZjbeZp_lhgbljbeZfb \ kibjlh \hf jZkl\hj_ ba[uldZ ]b^jhdkb^Z gZljby k h[jZah\Zgb _f [bkZgljZgbeh\ ko_fZ 16).
>@ >@

144


Jhk obf ` @ Jhk obf h[-\Z bf > B F_g^_e__\Z




l



L





3


X + O­ N O Ar X O N
]^_ O
+

Ar N+ O­ O

CH C

2

N Ar O N

Zp_lhgbljbevghc ]jmii_ ijb\h^bl d iheghfm bg]b[bjh \Zgbx p_e_\h]h ijhp_kkZ < j_amevlZl_ j_Zdpbb -oehj6-nlhjn_gbeZp_lhgbljbeZ k -]Zeh]_ggbljh[_gaheZfb [ue ihemq_g ijh^mdl gmde_hnbevgh]h aZf_s_gby ]Zeh ]_gZ ko_fZ 17).


Cl

NO2 NaOH

Cl

C

N

+
CN

ROH F R NO2

Ar = Ph, 3-ClC6H4, 4-CH3C6H4, 2-CH3OC6H4, 4-CH3OC6H4, 3,4-(CH3O)2C6H3
O O

= ijhklZy k\yav, O, S, CH2, -CC-, -CH=CH-, >C=O, -S-S-, ,
O

]^_

F
5 &O %U

>C=CCl2,
O O

, ,

O

O

, ,

N
S

N O

,
S

S

GZ hkgh\Zgbb ijh\_^_gguo bkke_^h\Zgbc knhjfm ebjh\Zgu hkgh\gu_ lj_[h\Zgby d kljmdlmj_ gbljhkm[ kljZlZ ^ey kbgl_aZ -[_gabahdkZaheh\ Z g_h[oh^bfh gZebqb_ aZf_klbl_ey \ iZjZ-iheh`_gbb d gbljh]jmii_ [ gbljhkh_^bg_gb_ g_ ^he`gh ijhy\eylv k\hckl\ CH-, NH- beb -dbkehl \ mkeh\byo j_Zdpbb \ aZf_klbl_ev g_ ^he`_g [ulv hq_gv Zdlb\guf gmd e_hnm]hf \ j_Zdpbb ] aZf_klbl_ev g_ ^he`_g kha^Z\Zlv ^hihegbl_evguo j_Zdpbhgguo p_gljh\ IhdZaZgh qlh hl kljh_gby j_Z]_glZ ZjbeZp_lhgbl jbeh\ kbevgh aZ\bkbl oh^ j_Zdpbb LZd \\_^_gb_ fgh ]bo aZf_klbl_e_c \ ZjhfZlbq_kdh_ y^jh n_gbeZp_lhgbl jbeZ ijb\h^bl d kgb`_gbx \uoh^Z p_e_\uo \_s_kl\ qlh k\yaZgh k ijhl_dZgb_f iZjZee_evguo ijhp_kkh\ h[jZah\Zgby ih[hqguo ijh^mdlh\ Ke_^m_l ih^ q_jdgmlv qlh ijb \aZbfh^_ckl\bb -gbljhoehj[_gaheZ k n_gbeZp_lhgbljbehf g_ gZ[ex^Z_lky nhjfbjh\Zgby dZdbo-eb[h \_s_kl\ ihfbfh -oehj-3-n_gbe-2,1-[_gabahdkZaheZ Dbg_lbq_kdb_ bkke_^h\Zgby ijh\_^_ggu_ gZ fh ^_evguo kh_^bg_gbyo iha\hebeb k^_eZlv h[hkgh\Zggh_ ij_^iheh`_gb_ h ebfblbjmxs_c klZ^bb ijhp_kkZ dh lhjhc y\ey_lky h[jZah\Zgb_ /-dhfie_dkZ < kemqZ_ \\_^_gby \ j_Zdpbx aZf_s_gguo n_gbeZp_lhgbljbeh\ fh`_l ijhbkoh^blv \ujZ\gb\Zgb_ kdhjhkl_c hl^_evguo klZ^bc beb kf_s_gb_ ebfblbjmxs_c klZ^bb Wlh b \ujZ`Z_lky \ kgb`_gbb \uoh^Z p_e_\uo ZgljZgbeh\ \ h[jZah\Zgbb kfhehh[jZaguo ijbf_k_c Z lZd`_ \ nhj fbjh\Zgbb ih[hqguo fbghjguo ijh^mdlh\ Kgb`_gb_ \uoh^Z ZgljZgbeh\ hkh[_ggh aZf_lgh ijb bkihevah\Z gbb hjlh-aZf_s_gguo n_gbeZp_lhgbljbeh\ <\_^_gb_ ^\mo ^Z`_ g_[hevrbo ih h[t_fm aZf_klb l_e_c Zlhfu oehjZ b nlhjZ \ h[Z hjlh-iheh`_gby d
>@   2+    >@  

Ko_fZ



J_amevlZlu d\Zglh\hobfbq_kdh]h fh^_ebjh\Zgby f_lh^ :F /-dhfie_dkZ ijh^mdlZ ijbkh_^bg_gby gmde_hnbeZ d Zlhfm m]e_jh^Z ZjhfZlbq_kdh]h y^jZ k\yaZggh]h k \h^hjh^hf b Hlg-dhfie_dkZ ijh^mdlZ ijbkh_^bg_gby gmde_hnbeZ d Zlhfm m]e_jh^Z ZjhfZlb q_kdh]h y^jZ k\yaZggh]h k ]Zeh]_ghf k\b^_l_evkl\mxl qlh ^Zggu_ bgl_jf_^bZlu g_agZqbl_evgh jZaebqZxlky ih wg_j]_lbq_kdbf oZjZdl_jbklbdZf Hf(/) = ­21,99 ddZe fhev Hf(Cl) = ­21,23 ddZe fhev ihwlhfm ijbqbgZ ijhl_dZgby j_Zdpbb aZf_s_gby ]Zeh]_gZ Z g_ \h^hjh^Z aZdexqZ_lky \ agZqbl_evguo aZljm^g_gbyo dhlhju_ \hagbdZxl ijb ^Zevg_crbo ij_\jZs_gbyo /-dhfie_dkZ \ ZgljZgbe Ijb bkihevah\Zgby ZjbeZp_lhgbljbeh\ kh^_j`Zsbo kbevgu_ we_dljhghZdp_ilhjgu_ ]jmiiu gbljh- ljbnlhjf_lbevgZy gZ[ex^Z_lky j_adh_ kgb`_gb_ kdhjh klb hkgh\ghc j_Zdpbb b ij_h[eZ^Zgb_ ih[hqguo ijh p_kkh\ < kemqZ_ -gbljhn_gbeZp_lhgbljbeZ b ljbnlhjf_lben_gbeZp_lhgbljbeZ g_ m^Zehkv \u^_eblv ba j_Zdpbhgghc fZkku p_e_\u_ kh_^bg_gby >ey kha^Zgby [he__ ihegh]h ij_^klZ\e_gby h f_oZ gbaf_ bkke_^m_fh]h ijhp_kkZ g_h[oh^bfh \u^_e_gb_ ih[hqguo ijh^mdlh\ b bamq_gb_ bo kljmdlmju GZjZ\g_ k bamq_gb_f dbg_lbq_kdbo aZdhghf_jghkl_c h^gbf ba deZkkbq_kdbo f_lh^h\ \uykg_gby imlb fgh]hklZ^bcguo \aZbfh^_ckl\bc y\ey_lky \u^_e_gb_ \ bg^b\b^mZevghf khklhygbb b mklZgh\e_gb_ kljh_gby fbghjguo ijh^md lh\ >Zggu_ \_s_kl\Z k\b^_l_evkl\mxl h gZebqbb \ j_Zdpbhgghc kbkl_f_ dexq_\uo bgl_jf_^bZlh\ hl dh lhjuo [_jml gZqZeh ih[hqgu_ ijhp_kku KjZ\gbl_ev guc ZgZeba fbghjguo ijh^mdlh\ deZkkbnbdZpby mklZ gh\e_gb_ baf_g_gbc khhlghr_gby hkgh\ghc fbghjguc ijh^mdlu \ aZ\bkbfhklb hl mkeh\bc j_Zdpbb hkh[_ggh g_aZf_gbf ijb bamq_gbb \ebygby kljmdlmju bkoh^guo \_s_kl\ gZ ijhl_dZgb_ ijhp_kkZ H ijbkmlkl\bb \ j_Zd pbhgghc fZkk_ ih^h[gh]h bgl_jf_^bZlZ k\b^_l_evkl\m _l lh qlh j_Zdpby ]Zeh]_ggbljh[_gaheh\ k f_lhdkbn_ gbeZp_lhgbljbeZfb aZ\_jrZ_lky h[jZah\Zgb_f kf_kb \_s_kl\ ko_fZ 18). Hkgh\gufb ijh^mdlZfb j_Zdpbb y\eyxlky khhl\_l kl\mxsb_ -[_gabahdkZaheu gh h[jZamxlky lZd`_ aZf_s_ggu_ [_gahcgu_ dbkehlu b kh_^bg_gby jy^Z 9-pbZgh-10-Zdjb^bg-N-hdkb^Z
      >@

Ko_fZ

7

145


< X Hjeh\ : > Dhlh\ < < =Zg`Z : B JmkZdh\


X NO CN
2

X
>=D-PrOH Na OH

N O + NC N+ O
­

C O OH

+ R' X R

+ R' R

R' R
]^_

R'

R

R = OCH3, R = H, R = R = OCH3; X = Cl, Br, I.

?s_ h^gbf ijbf_jhf k\b^_l_evkl\mxsbf \ ihevam kms_kl\h\Zgby ]bihl_lbq_kdh]h dexq_\h]h bgl_jf_^bZ lZ Z lZd`_ ihdZau\Zxsbf _]h \ukhdmx eZ[bevghklv y\ey_lky lh qlh ijb \aZbfh^_ckl\bb -gbljhoehj[_gaheZ k -^boehjn_gbeZp_lhgbljbehf ihemqZxlky ^\Z ijh^mdlZ ijb[ebabl_evgh \ jZ\ghf khhlghr_gbb ko_fZ 19).
>@

Ko_fZ

CN

NO

2

CH

2

N

O + Cl

+ Cl Cl Cl + Cl N HO Cl O

>=D-PrOH N aO H
Cl Cl Cl Cl

Cl

Ko_fZ
X


X

LZdbf h[jZahf j_amevlZlu bamq_gby ijh^mdlh\ \aZbfh^_ckl\by gbljhZj_gh\ k ZjbeZp_lhgbljbeZfb k\b^_l_evkl\mxl h lhf qlh kljmdlmjZ ihke_^gbo hdZau \Z_l agZqbl_evgh_ \ebygb_ gZ ijhl_dZgb_ ijhp_kkZ < g_dhlhjuo kemqZyo hgh gZklhevdh yjdh \ujZ`_gh qlh fbghjgu_ ijh^mdlu ijbkmlkl\mxl \ j_Zdpbhgghc fZkk_ \ [hevr_f dhebq_kl\_ q_f -[_gabahdkZaheu >ey 4-gbljhoehj[_gaheZ b n_gbeZp_lhgbljbeZ ^ZggZy klZ ^by y\ey_lky kdhjhklvebfblbjmxs_c b ^Zevg_crb_ ij_\jZs_gby ijhbkoh^yl hq_gv [ukljh Ijb bkihevah \Zgbb ^jm]bo ZjbeZp_lhgbljbeh\ dZjlbgZ f_gy_lky Kljh_gb_ \u^_e_gguo fbghjguo ijh^mdlh\ k hq_ \b^ghklvx mdZau\Z_l gZ ijhl_dZgb_ _s_ h^ghc f_^e_g ghc klZ^bb hlijZ\ghc lhqdhc dhlhjhc km^y ih \k_fm y\ey_lky ZgbhggZy nhjfZ ZjbepbZghf_lbe_gh-obghgfhghhdkbfZ Hl g_]h [_jml gZqZeh g_kdhevdh hl\_l\e_gbc iZjZee_evguo hkgh\ghfm imlb qlh k\yaZ gh k \hafh`ghklvx ij_[u\Zgby dexq_\h]h bgl_jf_^bZ lZ \ g_kdhevdbo kl_j_hbahf_jguo nhjfZo ko_fZ 20). >Zggh_ ij_^iheh`_gb_ ih^l\_j`^Z_lky l_f nZdlhf qlh ^ey n_gbepbZghf_lbe_g-i-obghghdkbfh\ f_lh^hf YFJ 1G ki_dljhkdhibb mklZgh\e_gh gZebqb_ kl_j_h




O N X O
­

­

N X CN

CN

NC

N O
­

NC

NO

­

R' R R' R R' R

R' R

NO R X R' X

O N

­ +

R R R' R' C O OH

CN

Ko_fZ
146

20


Jhk obf ` @ Jhk obf h[-\Z bf > B F_g^_e__\Z




l



L





3

N

O

X

+ .
X=OAlk, OH

X=H

+ .

N

O

R

N

O

+ .

R N

R

+ .
N

+ .

+ .

R O R

+ .
Ko_fZ

21

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> @ >@

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147


< X Hjeh\ : > Dhlh\ < < =Zg`Z : B JmkZdh\


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H N

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[H] N O Ph
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N O R Ar
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13. 14. 15.

CC
17. 18.

Fbevlh < B Hjeh\ < X Fbjhgh\ = K Ba\ \ukr mq_[ aZ\_^_gbc Obfby b obf l_ogh l \ui k --98. eh]by Fbevlh < B Hjeh\ < X Fbjhgh\ = K Dbg_lbdZ b dZlZeba l k --4. Fbevlh < B Hjeh\ < X Fbjhgh\ = K Obfb q_kdZy l_ogheh]by k --26. Fbevlh < B Hjeh\ < X Fbjhgh\ = K Ba\ \ukr mq_[ aZ\_^_gbc Obfby b obf l_ogh eh]by l \ui k --111. Hjeh\ < X DjbgbpugZ = < Fbevlh < B ;Zrdbjkdbc obfbq_kdbc `mjgZe k --103. :\l k\b^ KKKJ de K








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FhjhrdbgZ ? G :\lhj_n ^bkk dZg^ obf gZmd YjhkeZ\ev k 19. Hjeh\ < X Dhlh\ : > =Zg`Z < < Khdh eh\ < = D_kZj_\Z L < L_a ^hde F_` ^mg gZmqgh-l_og dhgn Obfbq_kdb_ j_Zd lb\u j_Z]_glu b ijhp_kku fZehlhggZ`ghc obfbb MnZ
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21.

Dhlh\ : > Hjeh\ < X Dhi_cdbg < < \ukr mq_[ aZ\_^_gbc Obfby b obf l \ui -- k --59. Hjeh\ < X Dhlh\ : > ;ukljydh\Z ? Fbjhgh\ = K @ hj]Zg obfbb l


Fbjhgh\ = K Ba\ l_ogheh]by










; Dhi_cdbg < < \ui k --




1410. 22.



=Zg`Z < < :\lhj_n ^bkk k




dZg^ obf gZmd YjhkeZ\ev


23. Davis R.B., Pizzini L.C. J. Amer. Chem. Soc., 1960, v. 25, p. 1884. 24. Dhlh\ :> Hjeh\

25. 26.

EBL?J:LMJ:
1.

Dhlh\ : > Hjeh\ < X =Zg`Z < < Khdheh\ < = D_kZ j_\Z L < L_a ^hde F_`^mg gZmqgh-l_og dhgn
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Obfbq_kdb_ j_Zdlb\u j_Z]_glu b ijhp_kku fZehlhggZ` ghc obfbbª Fbgkd--MnZ k

27.

2.

L_hj_lbq_kdZy hj]Zgbq_kdZy obfby F Ba^Zlbgebl k


;Zgg_l > N

28. 29. 30.

3. Terrier F. Nucleophilic aromatic displacement: the influence of nitrogroup. VCH Publishers, Inc., 1991, j.460. 4. Cervera M., Jordi M., Xavier M. Tetrahedron, 1996, v. 52, S --2564. 5. Fbevlh
31. 32.

\ukr mq_[ aZ\_^_gbc Obfby b obf l_ogheh]by l \ui k --65. Fbevlh < B Hjeh\ < X Fbjhgh\ = K Dhi_cdbg < < Dbg_lbdZ b dZlZeba l k --525. :[jZfh\ B = IeZolbgkdbc < < Ba\ \ukr mq_[ aZ\_^_ gbc Obfby b obf l_ogheh]by l \ui k






33.



9. Vlasov V., Khalfina I.A. Book of Abst. Of Conf. «Reaction mechanisms and Oganic Intermediates». S-3HWHUEXUJ j 10. OZenbgZ B:
34.

\ui k OZenbgZ B : ;_j_]h\Zy B <

Ba\ \ukr mq_[ aZ\_^_gbc Obfby b obf l_ogheh]by l \ui k --33. Hjeh\ < X Dhlh\ : > Khdh\bdh\ Y < @ hj]Zg obfbb l \ui k --111. Dhlh\ : > Hjeh\ < X ;ukljydh\Z ? ; Dhi_cdbg < < Ba\ \ukr mq_[ aZ\_^_gbc Obfby b obf l_ogheh]by l \ui k --82. Hjeh\ < X Dhlh\ : > JmkZdh\ : B ;ukljydh\Z ? ; Dhi_cdbg < < Fbjhgh\ = K @ hj]Zg obfbb l \ui k --574. Dhlh\ : > :\lhj_n ^bkk ^-jZ obf gZmd F k Hjeh\ < X Khdh\bdh\ Y < Dhlh\ : > KlZjbdh\ : : @ hj]Zg obfbb l \ui k --1791. Hjeh\ < X Dhlh\ : > =Zg`Z < < Fbjhgh\ = K Ba\ \ukr mq_[ aZ\_^_gbc Obfby b obf l_ogheh]by l \ui k --101. Dhlh\ : > Hjeh\ < X Hjeh\Z L G Dhi_cdbg < < LZf `_ l \ui --2, k --63. Hjeh\ < X Dhlh\ : > Dhi_cdbg < < Hjeh\Z L G JmkZ dh\ : B Fbjhgh\ = K @ hj]Zg obfbb l \ui k --1381. Hjeh\ < X Dhlh\ : > ;ukljydh\Z ? ; Khdh\bdh\ Y < Ba\ \ukr mq_[ aZ\_^_gbc Obfby b obf l_ogheh]by, l \ui k --19. Fbjhgh\ = K Dhlh\ : > Hjeh\ < X JmkZdh\ : B





149


< X Hjeh\ : > Dhlh\ < < =Zg`Z : B JmkZdh\


35.

36. 37. 38. 39. 40.

Hjeh\ < X Dhlh\ : > =Zg`Z < < KlZjbdh\ : : JmkZdh\ : B Ba\ \ukr mq_[ aZ\_^_gbc Obfby b obf l_ogheh]by l \ui k --8. Hjeh\ < X Dhlh\ : > =Zg`Z < < Fbjhgh\ = K @ --1744. hj]Zg obfbb l \ui k Hjeh\ < X =Zg`Z < < Dhlh\ : > LZf `_ l \ui k Hjeh\ < X Khdh\bdh\ Y < Dhlh\ : > Obfbq_kdZy l_o gheh]by k --40. Hjeh\ < X Dhlh\ : > Hjeh\Z L G =Zg`Z < < Obfby --736. ]_l_jhpbde kh_^ k R\ujdh\Z G K Dhlh\ : > Hjeh\ < X KhjhdbgZ L : K[ lj Kh\j_f_ggu_ ijh[e_fu [bheh]bb obfbb wdheh ]bb b wdheh]bq_kdh]h h[jZah\Zgby YjhkeZ\ev k --345.
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41. 42.

43.

Khdh\bdh\ Y < Khdh\bdh\Z B G Dhlh\ : > Hjeh\ < X Lhdkbdhe \_klgbd --33. Dhi_cdbg < < DZaZgkdbc K F Dhlh\ : > Hjeh\ < X L_a ^hde kh\_s Gh\hklb we_dljhobfbb hj]Zgbq_ kdbo kh_^bg_gbc LZf[h\ k --12. =Zg`Z < < Dhlh\ : > Hjeh\ < X K[ lj Kh\j_f_ggu_ ijh[e_fu [bheh]bb obfbb wdheh]bb b wdheh]bq_kdh]h h[ jZah\Zgby YjhkeZ\ev k --324.
F ;,,, © ª © ª

44. Orlov V.Yu., Kotov A.D., Ganzha V.V., Sokolov V.G. 0HQGHOHHY FRPPXQ j --38. 45. Hjeh\ ;ukljydh\Z ?; Dhi_cdbg <<

K[ lj DZj[hgbevgu_ kh_^bg_gby \ kbgl_a_ ]_l_jhpbd eh\ KZjZlh\ k
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46. Orlov V.Yu., Kotov A.D., Budanov N.A. Mendeleev Commun., 2000, p. 76--77.

150