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1996•Journal of the American Chemical SocietyRequires access

Reactivity of Carbenes and Ketenes in Low-Temperature Matrices. Carbene CO Trapping, Wolff Rearrangement, and Ketene−Pyridine Ylide (Zwitterion) Observation

Peter Visser, Ralf Zuhse, Ming Wah Wong, Curt Wentrup

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Abstract

Dicarbalkoxyketenes 8a and 8b are obtained by photolysis of diazo esters 7 in cryogenic matrices or by FVT of 7 followed by matrix isolation. The photochemical Wolff rearrangement of diazomalonates 1 in Ar matrix at temperatures as low as 6.5 K produces alkoxy(alkoxycarbonyl)ketenes 3, also obtained by FVT of 1 . Photolysis of 1 in CO matrix at ≥6.5 K produces the dicarbalkoxyketenes 8 . Ketenes 3, 8, and 12 react with pyridine above 40 K to produce ketene−pyridine ylides (zwitterions) 9, 10, and 13, respectively.

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Dicarbalkoxyketenes 8a and 8b are obtained by photolysis of diazo esters 7 in cryogenic matrices or by FVT of 7 followed by matrix isolation. The photochemical Wolff rearrangement of diazomalonates 1 in Ar matrix at temperatures as low as 6.5 K produces alkoxy(alkoxycarbonyl)ketenes 3, also obtained by FVT of 1 . Photolysis of 1 in CO matrix at ≥6.5 K produces the dicarbalkoxyketenes 8 . Ketenes 3, 8, and 12 react with pyridine above 40 K to produce ketene−pyridine ylides (zwitterions) 9, 10, and 13, respectively.

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Available abstract

Dicarbalkoxyketenes 8a and 8b are obtained by photolysis of diazo esters 7 in cryogenic matrices or by FVT of 7 followed by matrix isolation. The photochemical Wolff rearrangement of diazomalonates 1 in Ar matrix at temperatures as low as 6.5 K produces alkoxy(alkoxycarbonyl)ketenes 3, also obtained by FVT of 1 . Photolysis of 1 in CO matrix at ≥6.5 K produces the dicarbalkoxyketenes 8 . Ketenes 3, 8, and 12 react with pyridine above 40 K to produce ketene−pyridine ylides (zwitterions) 9, 10, and 13, respectively.

Key concepts: Ketene, Chemistry, Wolff rearrangement, Carbene, Ylide, Pyridine, Zwitterion, Photochemistry

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Reactivity of Carbenes and Ketenes in Low-Temperature Matrices. Carbene CO Trapping, Wolff Rearrangement, and Ketene−Pyridine Ylide (Zwitterion) Observation — Research Paper | ScholarLens