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Letters in Organic Chemistry
Volumn 4, Issue 5, 2007, Pages 319-321
A mild synthesis of nitriles by TPPX2-promoted dehydration of primary amides
Author keywords

Dehydration; Dehydrohalogenation; Halotriphenoxy phosphonium halides; Imidoyl halides; Nitriles; Phosphonium salts
Indexed keywords

EID: 36148934488     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017807781212157     Document Type: Article
Times cited : (6)
References (29)
  • 23
    • 0000655751 scopus 로고
    • Trost, B.M, Fleming, I, Eds, Pergamon
    • Kantlehner, W. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I., Eds.; Pergamon, 1991; Vol. 6, pp. 485-599.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 485-599
    • Kantlehner, W.1
  • 24
    • 36148969065 scopus 로고    scopus 로고
    • 2. Chlorine was bubbled into a solution of triphenyl phosphite (1.85 mL, 7.0 mmol) in anhydrous chloroform (20 mL) at-30°C until the solution became lemon yellow; a few more drops of triphenyl phosphite were added until the solution turned colour-less again. After addition of anhydrous triethylamine (2.0 mL, 14.6 mmol), the appropriate amide 1 (5.8 mmol) was added, and the resulting suspension was stirred for 16 hr while warming to room temperature. The reaction mixture was then concentrated under reduced pressure and the crude residue was purified by silica gel chromatography to yield the desired nitrile 2.
    • 2. Chlorine was bubbled into a solution of triphenyl phosphite (1.85 mL, 7.0 mmol) in anhydrous chloroform (20 mL) at-30°C until the solution became lemon yellow; a few more drops of triphenyl phosphite were added until the solution turned colour-less again. After addition of anhydrous triethylamine (2.0 mL, 14.6 mmol), the appropriate amide 1 (5.8 mmol) was added, and the resulting suspension was stirred for 16 hr while warming to room temperature. The reaction mixture was then concentrated under reduced pressure and the crude residue was purified by silica gel chromatography to yield the desired nitrile 2.
  • 26
    • 0029051023 scopus 로고    scopus 로고
    • Synthesis of (R)-2-Phenylpropionitrile (2h) with TPPBr2. Bromine (123 μL, 2.4 mmol) was added to a solution of triphenyl phosphite (629 μL, 2.4 mmol) in anhydrous chloroform (10 mL) maintained at -60°C, followed by addition of triethylamine (0.7 mL, 5.0 mmol, A solution of optically active propanamide (R)-1h (300 mg, 2.0 mmol, ee 51, in chloroform (3 mL) was then added, and the resulting clear solution was stirred while warming to room temperature. After 16 hr the reaction mixture was concentrated in vacuo and subjected to silica gel chromatography (using light petroleum/diethyl ether 9:1) to afford (R)-2-phenylpropionitrile (2h, 209 mg, 85, as a colourless oil, α]D, 9.5 c 2.4, CHCl3, lit, 18.5, ee ≥95, Enders, D, Plant, A, Backhaus, D, Reinhold, U. Tetrahedron, 1995, 51, 10699
    • 3), lit. +18.5, ee ≥95%; Enders, D.; Plant, A.; Backhaus, D.; Reinhold, U. Tetrahedron, 1995, 51, 10699.
  • 27
    • 36148946154 scopus 로고    scopus 로고
    • 13C NMR and MS spectroscopy, and by elemental analysis.
    • 13C NMR and MS spectroscopy, and by elemental analysis.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.