Доброе время суток, уважаемые химики!
Известно, что иодоформная реакция - на метилкетоны и соответствующие вторичные спирты. Еще известно явление винилогии. А можно ли провести синтез еще и по удаленным метильным группам в альфа,бета-непредельном карбонильном соединении, например, самое простое, что приходит на ум - окись мезитила
(СН3)2С=СН-С(О)СН3
Что можно при этом ожидать? По идее, исчерпывающее иодирование всех метильных групп и расщепление вплоть до пропандиовой кислоты и иодоформа.
Спасибо.
Особенности протекания иодоформной реакции
Re: Особенности протекания иодоформной реакции
US3994897
50 parts of mesityl oxide are added to a mixture of 900 parts by volume of sodium hypochlorite solution (containing 149 parts of sodium hypochlorite), 600 parts by volume of water and 0.5 part of sulfamide.
The solution turns cloudy and the temperature rises to 60.deg. C in the course of 10 minutes.
The mixture is then stirred for a further 3 hours after which 20 parts by volume of concentrated sodium bisulfite solution (38percent strength by weight) are added.
The organic phase is separated off and the aqueous solution is acidified and then extracted once with 150 parts by volume of chloroform.
The chloroform is distilled off the combined organic phases. 40 parts of β,β-dimethylacrylic acid (80percent of theory) melting at from 60.deg. to 63.deg. C are obtained. STR23
С ЙОдОм
Cuculescu
Bulet.Cernauti, 1927 , vol. 1, # I p. 53
With aqueous sodium hypochlorite
Pressman; Lucas
Journal of the American Chemical Society, 1940 , vol. 62, p. 2078
Smith; Prichard; Spillane
Organic Syntheses,
Barbier; Leser
Bulletin de la Societe Chimique de France, 1905 , vol. <3>33, p. 815
Sues
Justus Liebigs Annalen der Chemie, 1951 , vol. 571, p. 201,212
Madler, M. M.; Klucik, J.; Soell, P. S.; Brown, C. W.; Liu, S.; et al.
Organic Preparations and Procedures International, 1998 , vol. 30, # 2 p. 230 - 234
Salov, V. N.; Zil'berman, E. N.; Usova, N. Yu.
Zhurnal Organicheskoi Khimii, 1983 , vol. 19, # 10 p. 1778 - 1780
Kajigaeshi, Shoji; Nakagawa, Takashi; Nagasaki, Noritaka; Fujisaki, Shizuo
Synthesis, 1985 , # 6/7 p. 674 - 675
50 parts of mesityl oxide are added to a mixture of 900 parts by volume of sodium hypochlorite solution (containing 149 parts of sodium hypochlorite), 600 parts by volume of water and 0.5 part of sulfamide.
The solution turns cloudy and the temperature rises to 60.deg. C in the course of 10 minutes.
The mixture is then stirred for a further 3 hours after which 20 parts by volume of concentrated sodium bisulfite solution (38percent strength by weight) are added.
The organic phase is separated off and the aqueous solution is acidified and then extracted once with 150 parts by volume of chloroform.
The chloroform is distilled off the combined organic phases. 40 parts of β,β-dimethylacrylic acid (80percent of theory) melting at from 60.deg. to 63.deg. C are obtained. STR23
С ЙОдОм
Cuculescu
Bulet.Cernauti, 1927 , vol. 1, # I p. 53
With aqueous sodium hypochlorite
Pressman; Lucas
Journal of the American Chemical Society, 1940 , vol. 62, p. 2078
Smith; Prichard; Spillane
Organic Syntheses,
Barbier; Leser
Bulletin de la Societe Chimique de France, 1905 , vol. <3>33, p. 815
Sues
Justus Liebigs Annalen der Chemie, 1951 , vol. 571, p. 201,212
Madler, M. M.; Klucik, J.; Soell, P. S.; Brown, C. W.; Liu, S.; et al.
Organic Preparations and Procedures International, 1998 , vol. 30, # 2 p. 230 - 234
Salov, V. N.; Zil'berman, E. N.; Usova, N. Yu.
Zhurnal Organicheskoi Khimii, 1983 , vol. 19, # 10 p. 1778 - 1780
Kajigaeshi, Shoji; Nakagawa, Takashi; Nagasaki, Noritaka; Fujisaki, Shizuo
Synthesis, 1985 , # 6/7 p. 674 - 675
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