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Volumn 62, Issue 24, 1997, Pages 8361-8365

Palladium-Catalyzed Carbonylative Lactonization of Propargyl Alcohols with Organic Dichalcogenides and Carbon Monoxide

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EID: 0001090343     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970973q     Document Type: Article
Times cited : (89)

References (72)
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    • note
    • 2 was ineffective (the yield of 6a was 17%).
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    • 4 easily proceeds even at room temperature, see: (a) Zanella, R.; Ros, R.; Graziani, M. Inorg. Chem. 1973, 12, 2736. (b) Rauchfuss, T. B.; Shu, J. S.; Roundhill, D. M. Inorg. Chem. 1976, 15, 2096.
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    • 4 easily proceeds even at room temperature, see: (a) Zanella, R.; Ros, R.; Graziani, M. Inorg. Chem. 1973, 12, 2736. (b) Rauchfuss, T. B.; Shu, J. S.; Roundhill, D. M. Inorg. Chem. 1976, 15, 2096.
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    • note
    • 4 (0.02 mmol) under Pressure of CO (60 atm) at 80 °C for 39 h gave (Z)-1,3-bis(phenylthio)-2-nonen-1-one stereoselectively in 84% yield; see ref 5i.
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    • note
    • 1H NMR spectrometer, probably because five-membered cyclization proceeded very smoothly, compared with the six-membered cyclization.
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    • note
    • 2 to 1-octyne under similar reaction conditions (100 °C, 50 h) gave 1,3-bis(phenylseleno)-2-nonen-1-one in 57% yield (E/Z = 1/99) with the concomitant formation of some identified materials.
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    • In the absence of carbon monoxide, palladium-catalyzed decarbonylation occurred competitively. For a relating report, see: Wenkert, E.; Chianelli, D. J. Chem. Soc., Chem. Commun. 1991, 627 and ref 4m.
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