1979
DOI: 10.1021/jo00393a037
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Direct synthesis of .alpha.,.beta.-unsaturated nitriles from acetonitrile and carbonyl compounds: survey, crown effects, and experimental conditions

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Cited by 89 publications
(52 citation statements)
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“…This compound was obtained as a yellow solid: mp 109–111 °C (lit 33. 109–110 °C); 13 C NMR (100 MHz, CDCl 3 ) δ 88.6, 120.3, 120.4, 121.7, 125.5, 128.0, 128.5, 131.9, 132; HRMS m/z 203.07381 (calcd C 15 H 9 N, 203.07350).…”
Section: Methodsmentioning
confidence: 99%
“…This compound was obtained as a yellow solid: mp 109–111 °C (lit 33. 109–110 °C); 13 C NMR (100 MHz, CDCl 3 ) δ 88.6, 120.3, 120.4, 121.7, 125.5, 128.0, 128.5, 131.9, 132; HRMS m/z 203.07381 (calcd C 15 H 9 N, 203.07350).…”
Section: Methodsmentioning
confidence: 99%
“…The synthesis of starting materials, 2a-d, 2f, and 5, was carried out by Wittig reaction (Ph 3 P=CHCOOEt, benzene, reflux) of the corresponding salicyladehydes and the following propargylation with propargyl bromide (K 2 CO 3 /DMF, rt) or benzylation with 2-bromobenzyl bromide (K 2 CO 3 /DMF, rt). Other starting materials, 2e and 7, were prepared by sequential propargylation of salicyladehyde followed by Knoevenagel condensation reaction with CH 3 CN (KOH, reflux) 8 or with malononitrile (Ph 3 P, benzene, reflux). …”
Section: Methodsmentioning
confidence: 99%
“…[13] Cyanomethylenation of 8 in dioxane using the direct KOH-catalyzed condensation of acetonitrile with aromatic aldehydes, [14] followed by reduction of the resulting intermediate 9, gave the diaryl propanenitrile 10. Another alkyl nitrile chain was introduced via Friedel-Crafts acylation of 10, followed by reductive deoxygenation of the ketone function of the resulting intermediate 12, thus affording the dinitrile 13.…”
Section: Synthesis Of the Unsymmetrical Diaryldinitrile 14mentioning
confidence: 99%