N‐Arylisoindole

Kreher, Richard; Seubert, J.

doi:10.1002/ange.19660782114

Cited by 13 publications

(10 citation statements)

References 7 publications

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“…IR (KBr): v = 2960, 2790, 1643, 1610, 1485, 1290, 1231, 1158, 1021: ö = 4,54 (s; 3H , OCH,), 6,21 (s;1H,6,10 (m;8 H, ppm. - 300 MHz): ö = 4,63 (s; 3 H, O C H 3), 6,68 (s; 1H, H -l), 7,16-7,48 (m; 4H , H-2' bis H-6'), 7,57 (m (d), J16 = 7,7 Hz;1H,7,69,7,83 (2m(t); 2H, H-5, H-6), 7,96 (m (d), J45 = 7,5 Hz;1H,, 12,60 (s,verbreitert;1H,NH) (100), 219 (10), 214 (8), 208 (6),' 190 (5), 180 (18), 179 (5), 178 (6), 177 (5), 165 (8), 164 (7), 163 (5) C 16H 13F 3N 20 6S (418,34) Ber. C 45,94 H 3,13 N 6,69, Gef.…”

Section: -M Eth O X Y-1-( 4-m Ethylphenyl)-1 H-isoindoliummentioning

confidence: 99%

“…IR (KBr): v = 3120, 3080, 3040, 2990, 2910, 1670-1630, 1305, 1290-1225, 1215: ö = 2,29 (s; 3H , C H 3-4'), 2,47 (s; 3H , CH3-2'), 4,56 (s; 3H , O C H 3), 6,47 (s; 1H, H -l), 6,60 (m (d), Js.6. = 7,8 Hz;1H,6,91 (m (d), J6. 5.…”

Section: -M Eth O X Y-1-( 4-m Ethylphenyl)-1 H-isoindoliummentioning

confidence: 99%

“…C 45,72 H 3,15 N 6,67. IR (KBr): v = 3120, 3100-3020, 3000-2960, 2920, 1645, 1515, 1410, 1330, 1315, 1220, 1155, 1025 48;2H ,19,JAB = 8,6 Hz;2H ,7,52 (m (d); 1H, H-7), 7,71-7,77, 7,86-7,91 (2m; 1H, H-5, H -6), 8,03 (m (d), J45 = 7,9 Hz;1H,, 11,64 (s,verbreitert;1H,NH) C ]8H 18F 3N 0 4S (401,36) Ber. C 53, 87 H 4,52 N 3,49, Gef.…”

Section: -M Eth O X Y-1-( 4-m Ethylphenyl)-1 H-isoindoliummentioning

confidence: 99%

“…5. = 7,5 Hz; 1 H, H -6'), 7,09 (s; 1H, H-3'), 7,10 (m (d), J16 = 7,8 Hz;1H,7,69,7,82 (2m;2H ,7,96 (m (d), J45 = 7,8 Hz;1H,, 12,34 (s,verbreitert;1H,NH) (5), 102 (7), 95 (5), 77 (13, C6H 5), 69 (21, C F 3+). C 16H u F 3C13N 0 4S (476,68) Ber.…”

Section: -M Eth O X Y-1-( 4-m Ethylphenyl)-1 H-isoindoliumunclassified

“…Für die Entwicklung unabhängi ger Syntheseverfahren [7] ist die Tautom erie von 1H-und 2H-Isoindolen 1 und 3 von zentraler Be deutung.…”

Section: Introductionunclassified

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Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, XXXVIII [1,2] / Studies on the Chemistry of Isoindoles and Isoindolenines, XXXVIII [1,2]

Kreher

Hennige

Konrad³

et al. 1991

Zeitschrift Für Naturforschung B

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Substituted 3-Alkoxy-lH-isoindoles, Synthesis, Isolation, Spectroscopic Properties 3-Alkoxy-l H-isoindoles bearing substituents at the five-membered ring have been synthe sized starting with substituted isoindoline-l-ones via regiospecific O-alkylation with trialkyl oxonium tetrafluoroborates or alkyl trifluoromethanesulfonates and subsequent NHdeprotonation. The dependence of spectroscopic properties on the substituents has been inves tigated. The heterocyclic imidates exist exclusively in the benzenoid 1 H-structure; the tau to meric o-quinonoid 2H -form cannot be detected by spectroscopic means. Einleitung

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Section: -M Eth O X Y-1-( 4-m Ethylphenyl)-1 H-isoindoliummentioning

confidence: 99%

Section: -M Eth O X Y-1-( 4-m Ethylphenyl)-1 H-isoindoliummentioning

confidence: 99%

Section: -M Eth O X Y-1-( 4-m Ethylphenyl)-1 H-isoindoliummentioning

confidence: 99%

Section: -M Eth O X Y-1-( 4-m Ethylphenyl)-1 H-isoindoliumunclassified

“…Für die Entwicklung unabhängi ger Syntheseverfahren [7] ist die Tautom erie von 1H-und 2H-Isoindolen 1 und 3 von zentraler Be deutung.…”

Section: Introductionunclassified

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Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, XXXVIII [1,2] / Studies on the Chemistry of Isoindoles and Isoindolenines, XXXVIII [1,2]

Kreher

Hennige

Konrad³

et al. 1991

Zeitschrift Für Naturforschung B

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Isobenzofulvene

Häfner

Bauer

1968

Angewandte Chemie

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der Kettenmolekiile als Punkte. Die Rostebenen sind parallel zur b-Achse angeordnet. Der nachste Abstand fur zwei identische Rostebenen im orthorhombischen Gitter wurde aus den Rontgenreflexen zu 10,9 A berechnet. In Analogie zum Seidenfibroin ist anzunehmen, dab auch im Gitter der Poly-P-aminobuttersaure erst die ubernachste Rostebene rnit der ersten identisch ist, wie es die Zeichnung andeutet. Die Elementarzelle enthalt dann vier (3-Aminosaure-Einheiten. Die hieraus berechnete Kristalldichte stimmt mit der beobachteten gut uberein.Die Elementarzelle des Seidenfibroins "8,191 enthalt acht a-Aminosaureeinheiten. Der Unterschied in den Elementarzellen besteht im wesentlichen darin, daO beim Seidenfibroin erst eine Dipeptideinheit der Abmessung 7,O A zur Identitat in der Polypeptidkette fuhrt, wahrend bei Poly-$-aminobuttersaure bereits nach einer Einheit des Bausteins, also im Abstand von 4,6 A, die Identitat wiederkehrt.

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Isobenzofulvenes

Häfner

Bauer

1968

Angew. Chem. Int. Ed. Engl.

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azatriafulvalenium salts ( l o ) , m.p. 222 OC (dec.); h : : ; C N = 390 nm, log E = 1835 cm-1, ( I I a ) , m.p. 235 OC (dec.); A : : . " " = 372 nm, log E = 4.18; vc=c = 1840 cm-1, and ( I l b ) , m.p. 205 O C (dec.); h:F;CN = 362 nm (shoulder), log E = 4.09, vc=c = 1825 cm-1, are obtained in yields of 79, 50, and 59 % respectively. They are deprotonated t o give the 4.70; vc. Compound la1 (15) 115') (16d (16at) (166) (17) (18) Clop clop (10) (lla), R = H (Ilb), R = CsH5 azacalicenes (10') [ A : ! ; ' " = 384 nm, log E = 4.63; vc=c = 1835 cm-11. ( I l a ' ) [unstable red oil], and (11%) [dark red solution]; (10) and ( I l a ) by Hunig base in methylene chloride, ( I l b ) by potassium tert-butoxide. The action of tropylium perchlorate on 2,4-diphenylpyrrole under various conditions always gives a 1 : 2 adduct in a yield of about 15 %. This adduct can be isolated as the perchlorate ( I 2 ) , m.p. 282'C (dec.); = 554 nm, log E = 4.83. The free base is obtained from (12) with Hiinig base (m.p. 279OC; = 520 nm, log E = 4.67). Compound (12) gives a red-violet anion with potassium rert-butoxide. Yield ( %) 62 80 55 30 30 H Cl0,Q 265 [cl 187 226 [cl 208 174 235Benzoheterofulvalenes are obtained by reaction of pyrroles and indoles with the benzo-derivatives of the cations (11-13).The N a salt of 4,5-diphenylimidazole, which is prepared by heating diphenylimidazole with N a H in benzene in the presence of a little diglyme, reacts surprisingly smoothly with ( I ) and (2) in boiling benzene t o form the diazadithiafulvalenes (131 (red needles, m.p. 21OoC, yield 35 %) and (14) (m.p. 205 O C ; = 565 nm, log E = 4.60; yield 49 %). (14) forms a perchlorate [m.p. 280 "C (dec.); h:F;' " = 520 nm, log E = 4.571; reaction with an excess of perchloric 380 300-500 Id] 466 347 550 3 74 300-450 [d] 410 H acid gives the dication (14)2+ (h:~;cN-HC'04 = 460 nm, log E = 4.40). Compound (13) behaves in a similar manner.Di-and triphenylpyrroles react with benzophenone dichloride in acetonitrile at room temperature t o give the azafulvenes (15) and (16), which are isolated as the perchlorates and are deprotonated with Hunig base. In the presence of two equivalents of NaH, 4,5-diphenylimidazole reacts with benzophenone dichloride in boiling benzene t o give the tetraphenyldiazafulvene ( 1 71, which has already been synthesized by another route [3J, and with 2-methylthio-1,3-dithiolanylium methyl sulfate to form the 6,6-dithiodiazafulvene (18). log E 4.20 3.60 4.12 3.76 4.21 ca. 4 4.52 %position. 2,4-Diphenylpyrrole can be converted into the 0 analog (19) of a sesquifulvalene [m.p. 173 O C ; h:F;"" = 490 nm, log E = 4.64; yield 69 %. Perchlorate: m.p. 306 'C (dec.); = 499 nm, log E = 4.781 by heating in benzene with 4-methylthio-2,6-diphenylpyrylium perchlorate in the presence of one equivalent of NaH. (20) is obtained in the same way from 4,5-diphenylimidazole [m.p. = 227-228 O C ; h;!."" = 550, 518 nm. Perchlorate: m.p. 277 O C (dec.); = 507 nm. Dication: hCH3cN-HC104 max = 450 nm].

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N‐Arylisoindole

Abstract: 1,4,7-cyclodecatrienen ( I ) umsetzen. Analoge Reaktionen, wie wir sie fur das 4,5-Dimeth~l-cis,cis,rrans-l ,4,7-cyclodecatrien beschrieben haben [3J, fiihren von ( I ) und verwandten Verbindungen aus in guten Ausbeuten zu groBen Ringen.

Cited by 13 publications

References 7 publications

Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, XXXVIII [1,2] / Studies on the Chemistry of Isoindoles and Isoindolenines, XXXVIII [1,2]

Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, XXXVIII [1,2] / Studies on the Chemistry of Isoindoles and Isoindolenines, XXXVIII [1,2]

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