1959
DOI: 10.1002/cber.19590920116
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Über bi‐ und polycyclische Azulene, XXXVII. Synthesen und Eigenschaften von Azulen‐aldehyden

Abstract: 141 aus, der nach einigen Stunden abgesaugt, mit Wasser gewaschen und getrocknet wurde. Ausb. 25-36 % d. Th. Die Rohprodukte zersetzten sich bei 140-150". Durch mehrfaches Umkristallisieren aus Wasser erhielt man schwach gelbe Stabchen vom Zers.-P. 251". Das Bis-Semicarbazon gab keine Farbreaktion mit FeC13 und reduzierte Tillmans-Reagenz nicht. C10H16N603 (268.3) Ber. H 6.0 N 31.33 Gef. H 5.8 N 31.88Das gleiche Produkt wurde erhalten, wenn die ,,Verkochungs"-Losung unmittelbar (ohne Dehydrieren mit Benzochino… Show more

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Cited by 59 publications
(18 citation statements)
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“…Guaiazulene (1; 1.62 g; 8.17 mmol; Fluka; purified by CC) was formylated under Vilsmeier conditions in the usual way (cf. [I] [13]). The product was purified by CC on Al20, (Et20) and crystallized from acetone/hexane to yield 39 in wine-red crystals (1.38 g; 75%).…”
Section: Experimental Partmentioning
confidence: 96%
See 1 more Smart Citation
“…Guaiazulene (1; 1.62 g; 8.17 mmol; Fluka; purified by CC) was formylated under Vilsmeier conditions in the usual way (cf. [I] [13]). The product was purified by CC on Al20, (Et20) and crystallized from acetone/hexane to yield 39 in wine-red crystals (1.38 g; 75%).…”
Section: Experimental Partmentioning
confidence: 96%
“…See [I] [5] [7] [9]. I. Synthesis of 7-Isopropyl-1,3,4-trimethylazulene ( = 3-Methylguaiazulene; 2; cf: [13]). I.…”
Section: Experimental Partmentioning
confidence: 99%
“…(69) (cf. [35]). PCI, (6.25 g, 0.03 mol) was slowly added to DMF (30 mi 'J(H,H-C(7)) = 9.8, H-C (8) (7)); 2.822 (s, CH,-C(4)); 2.623 (s, CH,-C (6) (7)); 2.967 (s, CH,-C(4)); 2.708 (s, CH,-C(3)); 2.532 (s, CH3-C(6)).…”
Section: The Fragmentation Of the Molecular Ion ( M + ' )mentioning
confidence: 93%
“…3,4,6,8-TetramethylazuLne-l-carbaldehyde (78). According to [35], a Vilsmeier soh. was prepared by adding POCI, (3.2 g; 21.2 mmol) dropwise at 0" to DMF (10 ml).…”
Section: The Fragmentation Of the Molecular Ion ( M + ' )mentioning
confidence: 98%
“…[16] 4,8-Dideuterio-1-methylazulene (d 2 -10)f rom 4,8-dideutero-1-azulenylcarbaldehyde: [ All calculationsw ere performed using Beckes three-parameter hybrid functional [17] and the correlationf unctional of Lee,Y ang and Parr [18] (B3LYP) as implemented in Gaussian09. [19] The6 -311 + G-(d,p) basis set [20] was used for geometry optimizationand vibrational frequencyc alculations.…”
Section: Methodsmentioning
confidence: 99%