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Reaction of 2,2,4,4-Tetramethyl-3-thioxocyclobutanone with Dimethyl Diazomalonate Catalyzed by Rh2(OAc)4

Mlostoń G., Romański J., Heimgartner H.

Polish Journal of Chemistry

2002

Vol. 76 / nr 4

551-555

The reaction of 2,2,4,4-tetramethyl-3-thioxocyclobutanone (1) with dimethyl diazomalonate in the presence of Rh2(OAc)4 in toluene at 50_C yielded a mixture of three products 10, 11, and 12. Thiocarbonyl ylide 8 is believed to be the common intermediate. The formation of 10 is rationalized by the 1,3-dipolar electrocyclization of 8 to give spirocyclic thiirane 9, which spontaneously eliminated sulfur. On the other hand, the 1,5- dipolar electrocyclization of 8 led to 1,3-oxathiole 11, which is converted into lactone 12 by hydrolysis.

Reakcje związków siarko-organicznych z karbenami oraz karbenoidami

Mlostoń G.

LAB Laboratoria, Aparatura, Badania

2000

R. 5, nr 4

14-17

New insertion reactions of some carbenoids into amide- and sulfonamide-NH bonds

Mlostoń G., Celeda M., Świątek A., Kaegi M., Heimgartner H.

Polish Journal of Chemistry

1998

Vol. 72, nr 8

1907-1914

In the presence of catalytic amounts of Rh2(OAc)4 in toluene, dimethyl diazomalonate (1) decomposed with evolution of N2 to form a carbenoid of type 8 which reacted with carboxamides 2 and toluenesulfonamide (4) to,give 2-(acylamino)-and 2-(sulfonylamino)malonates 3 and 5, respectively. In an analogous reaction, alpha-diazo ketone 6 and 4 yielded N-(2-oxo-1, 2-diphenylethyl)toluenesulfonamide (7).