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Volumn 38, Issue 38, 1997, Pages 6689-6692

An efficient method for generation of α-oxoketenes: Cycloreversion of enolized Meldrum's acid derivatives

Author keywords

[No Author keywords available]

Indexed keywords

KETENE DERIVATIVE;

EID: 0030755320     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01566-9     Document Type: Article
Times cited : (50)

References (44)
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    • General procedure for preparation of 4: To a solution of 3 (3.0 mmol) in dichloromethane (10 ml) was added an ethereal solution of diazomethane (ca. 5 mmol) at -30 °C. The solution was stirred for 10 min and then evaporated in vacuo at -30 °C. Washing the crystalline residue with a mixture of ether and pentane afforded 4
    • General procedure for preparation of 4: To a solution of 3 (3.0 mmol) in dichloromethane (10 ml) was added an ethereal solution of diazomethane (ca. 5 mmol) at -30 °C. The solution was stirred for 10 min and then evaporated in vacuo at -30 °C. Washing the crystalline residue with a mixture of ether and pentane afforded 4.
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    • note
    • -1.
  • 23
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    • 3) δ 52.6, 125.7, 126.9, 127.4, 129.0, 166.5, 192.4
    • 3) δ 52.6, 125.7, 126.9, 127.4, 129.0, 166.5, 192.4.
  • 25
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    • General procedure for preparation of 8: A solution of 3 (3.0 mmol), t-butylchlorodiphenylsilane (3.3 mmol), and triethylamine (3.3 mmol) in dichloromethane (10 ml) was stirred at -50 °C for 2 h. The solution was evaporated in vacuo at below -20 °C. Ether was added to the residue and the solution was passed through a short column of silica gel cooled to -20 °C. Evaporation of the solvent at -20 °C followed by washing the crystalline residue with pentane furnished 8
    • General procedure for preparation of 8: A solution of 3 (3.0 mmol), t-butylchlorodiphenylsilane (3.3 mmol), and triethylamine (3.3 mmol) in dichloromethane (10 ml) was stirred at -50 °C for 2 h. The solution was evaporated in vacuo at below -20 °C. Ether was added to the residue and the solution was passed through a short column of silica gel cooled to -20 °C. Evaporation of the solvent at -20 °C followed by washing the crystalline residue with pentane furnished 8.
  • 26
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    • 3) δ 1.02 (6H, s), 1.09 (9H, s), 1.41 (9H, s), 7.3-7.5 (3H, m), 7.6-7.7 (2H, m)
    • 3) δ 1.02 (6H, s), 1.09 (9H, s), 1.41 (9H, s), 7.3-7.5 (3H, m), 7.6-7.7 (2H, m).
  • 27
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    • 3) δ 19.2, 23.7, 26.6, 30.7, 32.2, 93.1, 102.9, 128.0, 130.5, 132.1, 135.3, 160.5, 163.6
    • 3) δ 19.2, 23.7, 26.6, 30.7, 32.2, 93.1, 102.9, 128.0, 130.5, 132.1, 135.3, 160.5, 163.6.
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    • Fragmentation of Meldrum's acid and the derivatives to ketenes by flash vacuum pyrolysis (>400 °C) has been well studied. For reviews, see and a
    • Fragmentation of Meldrum's acid and the derivatives to ketenes by flash vacuum pyrolysis (>400 °C) has been well studied. For reviews, see: Wentrup, C. Pure Appl. Chem. 1996, 68, 891-894 and a.
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  • 44


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