4-Butyl-4 -cyan

Neben den beschriebenen Halogen-, Alkyl-, Alkoxy- und Nitro-Gruppen-substituierten Azobenzolen sind durch Kondensation von Fluor- und Cyan-substituierten Anilinen mit Nitroso-benzolen in saurer Losung auch 4-Butyl-4 -cyan-1, 4-Amino-3,5-difluor-2 und 4-Amino-2,3,5,6-tetrafluor-azobenzol3 zuganglich. 

Sulfimid S-Methyl-S-phenyl- Ell, 892 (aus R2S = N — Tos) Thioketen tert.-Butyl-cyan- Ell,... 

In vergleichbarer Weise spaltet das durch zweifache Addition von tert. Butyl-cyan-keten an 2-Dimethylamino-l, 3-thiazol erhaltliche Derivat I beim Erhitzen in Methanol ein Aquivalent des Ketens wieder ab1287 ... 

Benzo[c]furan, 1-cyan 0-3-phenyl-synthesis, 4, 683 Benzo[c]furan, 1,3-diatyl-cycloaddition reactions, 4, 635 reduction, 4, 614 synthesis, 4, 701 Benzo[c]furan, 1,3-di-t-butyl-synthesis, 4, 703 Benzo[c]furan, 1,3-dihydro-NMR, 4, 572-574, structure, 4, 549 synthesis, 4, 683 Benzo[c]furan, 4,7-dihydro-synthesis, 4, 682... 

Benzyl-(4-chlor-benzyliden)- 664 Bis-[fluoracetyl]- 239 Bis-[2-fluor-athyl]- 239 (Bis-[4-methoxy-phenyl]-methyl)- 377 Bis-[2-methyl-propyl]- 358 Bis-[2-phenyl-2-cyan-vinyl]- 58 tert.-Butyl-(hydroxy-tert.-butyl)-... 

Bis-[2-bcnzoyl-phcnyl]- 678 Bis-[4-tert.-butyl-benzyl)- 625 Bis-[cyan-mcthyl]- 703 Bis-[3,4-dichlor-benzyl]- 625 Bis-[diphenylmethyl]- 609 Bis-[4-methoxy-phcnyIJ- 625 Bis-[4-methyI-benzyl]- 625 Bis-[4-methyI-phenyI]- 625 Bis-[1 -naphthyl-(l )-iithyl]- 609 Bis-[3-oxo-butyI]- 585 Bis-[tridecafluor-hexyl]- 624 Cyanmcthyl- -chlorid 702 Dibenzyl- 622 Dicyclohexyl- 609 Didecyl- 623 f. 

Chlor-l-athoxycarbonylamino- 675 1 -Chlor-1 -butyl- 586 4-Chlor-4-methyl-l -tert.-butyl- 511 1-Chlor-l-nitro- 575 1-Chlor-1 -nitroso- 472 l-Chlor-2-oxo-l-athoxycarbonyl- 674 1-Cyanamino-1,2-dimethyl-105 Cyan- 109, 587 1 -Deutero-l-methyl-... 

Methyl-3-athoxycarbonyl- 650 l-Methyl-2-tert.-butyl- 651 1-Methyl- -chlorid 593 l-Methyl-2-cyan- 651 l-Methyl-3-cyan- 650 1-Organo- 91 ff. 

Cyan-l -(1,1,3,3-tetramethyl-butyl)-3-(l, 1,3,3-tctramethyl-butylamino)-4-(l, 1,3,3-tetrame-thyl-butylimino)-azetin setzt sich beim Kochen in Toluol unter Abspaltung von 2,4,4-Trimethyl-1-penten zu 5-Cyan-l-( 1,1,3,3-tetramethyl-butyl)-4-( 1,1,3,3-tetramethyl-hutylamino)-imidazol (80%) urn448. 

So wird aus 5-Chlor-937, 5-Brom-905 oder 5-Iod-l-methyl-4-nitro-imidazol905 durch Umsetzung mit Kaliumcyanid in Ethanol oder Dimethylformamid in Ausbeuten von 85, 68 bzw. 61% 5-Cyan-l-methyl-4-nitro-imidazol erhalten. Auch 5-Brom-l,2-dimethyl-4-nitro-938, 5-ChIor-l-ethyl-4-nitro-2-propyI-939 und l-Butyl-5-chlor-2-methyl-4-nitro-939 liefern 5-Cyan- 1,2-di-methyl-4-nitro-, 5-Cyan-l-ethyl-4-nitro-2-propyl- (81%) bzw. l-Butyl-5-cyan-2-methyl-4-nitro-imidazol (67%). 

Wird 1,2,3,4-Tetrahydro-benzofurazan-2-oxid mit substituierten Carbonsaure-arylamiden in Toluol unter RuckfluB erwarmt, erhalt man 5-(4-Cyan-butyl)-2,8-dioxa-l-aza-bi-cyclo[3.3.0]octan-3,4 6,7-bis-(dicarbonsiiure-arylamide)462 ... 

Bis-[trifluormethyl]-El, 263 E2, 264 Bis-[trifluormethyl]- -Anhydrid E2, 264 tert.-Butyl-phenyl- E2, 263 Cyan-(4-methoxy-phenyl)- -ethylester... 

Benzyl-diethoxy- E2, 134 Benzyl-diisopropyloxy- E2, 134 Benzyl-ethyl-phenyl- -tosylimid E2, 113 Benzyl-methyl-phenyl- -tosylimid E2, 113 Benzyloxy-diphenyl- E2, 17, 18 Benzyloxy-ethoxy-hydroxy- E2, 187 Bis-[2-biphenylyl]- E2, 876 [2,6-bis-(2-tetrahydropyranyloxy-methyl)-phenyl]-Bis-[4-brom-anilino]-phenyl- E2, 416 Bis-[2-brom-ethoxy]-(2-brom-ethyl)- E2, 196 Bis-[butylthio]-ethyi- E2, 79, 408 Bis-[2-chlor-cthoxy]-butyl- E2, 196 Bis-[2-chlor-ethoxy]-(2-chlor-ethyl)- E2, 196 Bis-[2-chlor-ethoxy]-methyl- E2, 196 Bis- 2-chlor-ethoxy]-phenyl- E2, 196, 197, 202 Bis- 2-ehlor-ethoxy]-(2-phcnyl-vinyl)- E2, 196 Bis-(2-ehlor-ethoxy]-vinyl- E2, 196 Bis-j 2-chlor-ethyl]-methyl- E2, 205 Bis-[chlormethyl]-dodecyl- E2, 22 Bis-12-cyan-ethyl]- E2, 223 Bis- diethylamino]-butyl- E2, 486 Bis-[ l-cthinyl-butyl]-phenyl- E2, 197 Bis-[ethoxycarbonyl-methyl]-chlor- E2, 251 Bis-[ethylthio]-ethyl- E2, 408 Bis-[4-methoxy-aniliiio]-phenyl- E2, 416 Bis-[4-methyl-phenylJ-phenyl- K2, 105 Bis- 4-methyl-phcnyl]-phenyl- -phenylsulfonvlimid E2, 105... 

Chlor-phenyl)-difluor- E2, 429 (4-Chlor-phenyl)-dimethoxy- E2, 197 Chlor-phenyl-propylthio- E2, 248 (2-Cyan-ethyl)-cyclohcxyl- E2, 245 Cyclohexyl-ethoxy-hydroxy- E2, 190 Dialkoxy-methyl- E2, 405 Dianilino-phenyl- E2, 416 Dibenzyloxy-phenyl- E2, 207 Dibrom-methyl- E2, 330, 331, 484 Dibrom-phenyl- E2, 30, 32 Dibutyl- E2, 263 Dibutyl-dicthylamino- E2, 287 Dibutyl-cthoxy- E2, 23 Dibutyl-ethoxy- E2, 23 Di-tert.-butyl-ethoxy- E2, 22 Di-tcrt.-butyl-methoxy- E2, 22 Dibutyloxy-ethyl- E2, 205 Dibutyloxy-naphthyl- E2, 203 Dibutyloxy-phenyl- E2, 207... 

Chlor-(2,4,6-tri-tert.-butyl-phenyl)- El. 273 Cholesleryloxy-hydroxv- XII/2, 6 (2-Cyan-ethyl)-dibenzyl- XII/1, 154 (2-Cyan-ethyl)-dioctyl- XII/1, 154 (1-Cyan-l-methyl-ethyloxy)-hydroxy- XII/2, 7 (4-Cyan-phenyl)-diphenyl- E2, 64 (2-Cyan-propyl)-diphenyl- E2, 10 1-Cyclohexenyl-diphenyl- E2, 13, 52 l-(l-Cyclohexenyl-ethyl)-diphenyl- E2, 72 (2-Cyclohexenyl-hydroxy-methyl)-hydroxy-X1I/1, 299... 

Acetamino-phenyl)-methyl- -ethylester E2, 200 (4-Acetoxy-butyl)-ethyl- - ethylester E2, 200 (3-Acetoxy-3-cyan-propyl)-mcthyl- -ethylester E2, 188... 

Bis-ftrimethylsilyloxy]-tris-[tiifluonnethyl]- E2, 877 Brom-cyan-triphenyi- XII/1, 129 Brom-hydroxy-triphcnyl- Xll/1, 127 (l-Brommethyl-pentyl)-tetrabrom- E2, 331 tert.-Butyl-tetrachlor- XII/1, 343 Butyl-tetrafluor- E2, 854... 

Aryloxy-2,3-dihydro- -2-oxid E2, 514 2-Butyl-2,3-dihydro- -2-oxid Xll/l, 535 5-Chlor-2-mercapto-2,3-dihydro- -2-sulfid-Pyri-dinium-Salz E2, 767 2-(2-Cyan-ethyl)-2-ethoxy- E2, 481 2-Cyclohexyl-2,3-dihydro- -2-oxid XII/I, 535 2-Ethoxy-2,3-dihydro- E2, 481 2-Ethoxy-2-(2-methoxycarbonyl-ethyl)- E2, 481 2-Mercapto-2,3-dihydro- -2-sulfid-Pyridinium-Salz E2, 767... 

The more substituted radicals continue to be measurably the more nucleophilic. The relative rates with which the various alkyl radicals react with the 4-cyan-opyridinium cation (7.33, Y = CN) and the 4-methoxypyridinium cation (7.33, Y = OMe) are given in Table 7.2. The LUMO of the former will obviously be lower than that of the latter. The most selective radical is the ferf-butyl, which reacts 350000 times more rapidly with the cyano compound than with the methoxy. This is because the ferf-butyl radical has the highest-energy SOMO, which interacts (B in Fig. 7.4) very well with the LUMO of the 4-cyanopyridi-nium ion, and not nearly so well (A) with the LUMO of the 4-methoxypyridinium ion. At the other end of the scale, the methyl radical has the lowest-energy SOMO, and hence the difference between the interactions C and D in Fig. 7.4 is not so great as for the corresponding interactions (A and B) of the ferf-butyl radical. Therefore, it is the least selective radical, reacting only 50 times more rapidly with the cyano compound than with the methoxy. 

Diazen l-tert.-Butyl-2-cyan- -1-oxid E16d, 134 (R - NO + NC—NH2/ Oxidat.)... 

Cyclopropan 1-Azido-l-dimethyl-amino- E17b, 1593 (OH - N3) Guanidin 4-Cyan-l-propyl- E4,1299 (OR - NH-C3H7) lH-Tetrazol 1-Butyl- E8d, 679 [HC(OR)3 + R-NH2/NaN3] 4H-1,2,4-Triazol... 

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