I. Ueber einen Kohlenwasserstoff C<sub>16</sub>H<sub>12</sub> aus Styrolenalkohol

Zincke, Th.; Breuer, A.

doi:10.1002/jlac.18842260104

Cited by 3 publications

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“…A little aldehyde was obtained in the liquid phase with 15-20 per cent H30 c6h6chohch2oh C6HbCH2CHO S1O2 (74 per cent) sulfuric acid (120, 811). However, the principal product was |3-phenylnaphthalene, which was obtained exclusively when 50 per cent sulfuric acid was used (812,813) and in yields as high as 60-70 per cent (121). With 48 per cent hydrobromic acid the yield of /3-phenylnaphthalene was 78 per cent (135).…”

Section: C6h5chohch2oh + Brch2ch(oc2h6)2mentioning

confidence: 99%

The Reactions of Monomeric Styrenes.

Everson¹

1949

Chem. Rev.

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Section: C6h5chohch2oh + Brch2ch(oc2h6)2mentioning

confidence: 99%

The Reactions of Monomeric Styrenes.

Everson¹

1949

Chem. Rev.

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“…Despite these limitations, several instances of the naphthalene type of cyclization have been observed. Perhaps the first case of aromatic cyclodehydration was encountered in 1884, when Zincke and Breuer (153) observed that phenylglycol or phenylacetaldehyde, in the presence of boiling 50 per cent sulfuric acid, yielded a hydrocarbon which was shown (154) to be /3-phenylnaphthalene. Zincke assumed, in the case of the phenylethylene glycol, that the reactions involved are dehydration to phenylacetaldehyde followed by aldol condensation of two molecules of phenylacetaldehyde, dehydration, and finally cyclization.…”

Section: A Naphthalene Systemmentioning

confidence: 99%

Aromatic Cyclodehydration.

Bradsher¹

1946

Chem. Rev.

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Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones via one-pot aryne acyl-alkylation/condensation

2009

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A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from b-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the b-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP.Synthetic chemists are constantly in search of new reaction sequences to convert simple, readily available starting materials into increasingly complex products. The most useful and economically valuable of these processes are able to do so quickly and with little operational difficulty. 1 It was with this concept in mind that we designed a procedure for the conversion of b-ketoesters to either 3-hydroxyisoquinolines or 2-hydroxy-1,4-naphthoquinones using a novel one-pot aryne acyl-alkylation/condensation sequence. Furthermore, when this process is coupled with a one-step synthesis of the b-ketoester substrates, it provides an exceptionally general two-step procedure for the conversion of readily available carboxylic acids to either of these important bicyclic aromatic structures. 2 Traditional approaches to the incorporation of these aromatic functionality within larger molecular scaffolds have typicallyThe Arnold and Mabel Beckman Laboratories of Chemical Synthesis, Division of Chemistry and Chemical Engineering, California Institute of Technology, 1200 E. California Boulevard, MC 164-30, Pasadena, CA 91125, USA. E-mail: stoltz@caltech.edu; Fax: +1 626 564 9297; Tel: +1 626 395 6064 † Electronic supplementary information (ESI) available: General experimental procedures, characterization data, NMR, and IR spectra. See DOI: 10.1039/b913336dScheme 1 Aryne acyl-alkylation followed by condensation with ammonia or intramolecular condensation and oxidation.relied upon transition metal-catalyzed cross coupling reactions employing C(sp 2 )-X precursors. 3 As an alternative to this strategy, we have been exploring methods to prepare various heteroaromatic systems via condensation of arynes with derivatives of carboxylic acids. 4 Following our report of a fluoride-induced insertion reaction between b-ketoesters (1) and arynes derived from silyl aryl triflates (2), 5 we began to investigate avenues by which the acyl-alkylated arene products (3) could be advanced toward larger ring systems (Scheme 1). 6 Our interest in nitrogencontaining heterocycles 7 led us to a report by Bentley et al., in which the synthesis of both 3-hydroxyisoquinolines (4) and 2-hydroxy-1,4-naphthoquinones (5) is accomplished by exposure of 1,5-ketoesters similar to 3 to either aqueous ammonia or alkaline base under an ambient atmosphere, respectively. 8 Indeed, we found that treatment of a crude acyl-alkylation reaction mixture containing methyl (2-acetylphenyl)acetate (3) with aqueous ammonium hydroxi...

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I. Ueber einen Kohlenwasserstoff C₁₆H₁₂ aus Styrolenalkohol

Cited by 3 publications

References 0 publications

The Reactions of Monomeric Styrenes.

The Reactions of Monomeric Styrenes.

Aromatic Cyclodehydration.

Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones via one-pot aryne acyl-alkylation/condensation

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I. Ueber einen Kohlenwasserstoff C16H12 aus Styrolenalkohol

Cited by 3 publications

References 0 publications

The Reactions of Monomeric Styrenes.

The Reactions of Monomeric Styrenes.

Aromatic Cyclodehydration.

Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones via one-pot aryne acyl-alkylation/condensation

Contact Info

Product

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I. Ueber einen Kohlenwasserstoff C₁₆H₁₂ aus Styrolenalkohol