Rearrangement of 1-aryl-2, 2-dihalo-1-alkanones

N De Kimpe, R Verhe, L De Buyck…

Index: Kimpe, Norbert De; Verhe, Roland; Buyck, Laurent De; Schamp, Niceas Journal of Organic Chemistry, 1980 , vol. 45, # 14 p. 2803 - 2813

Full Text: HTML

Citation Number: 15

Abstract

Reaction of l-aryl-2, 2-dichloro-l-alkanones with alkoxides in the corresponding alcohol afforded a mixture of l-aryl-2, 2-dialkoxy-l-alkanones and l-aryl-l, l-dialkoxy-2-alkanones. The mechanism was shown to proceed via a-chloro-a'-alkoxy epoxides, which rearranged into l- alkoxy-l-aryl-l-chloro-2-alkanones, the latter giving the final compounds via either another epoxide intermediate or a solvolysis mechanism. a, a-Dibromo-and a-bromo-a-chloroalkyl ...

Related Articles:

A simple procedure for the acetalization of carbonyl compounds

[Chan, T. H.; Brook, Michael A.; Chaly, T. Synthesis, 1983 , # 3 p. 203 - 205]

Selenium-catalyzed conversion of methyl ketones into. alpha.-keto acetals

[Tiecco, M.; Testaferri, L.; Tingoli, M.; Bartoli, D. Journal of Organic Chemistry, 1990 , vol. 55, # 15 p. 4523 - 4528]

Efficient preparation of α-ketoacetals

[Ayala-Mata, Francisco; Barrera-Mendoza, Citlalli; Jimenez-Vazquez, Hugo A.; Vargas-Diaz, Elena; Zepeda, L. Gerardo Molecules, 2012 , vol. 17, # 12 p. 13864 - 13878]

Novel Cerium (IV) Ammonium Nitrate Mediated Transformation of Styrenes to. ALPHA.-Methoxy Acetophenones.

[Nair, Vijay; Nair, Latha G.; Panicker, Sreeletha B.; Sheeba; Augustine, Anu Chemistry Letters, 2000 , # 6 p. 584 - 585]

Selenium-catalyzed conversion of methyl ketones into. alpha.-keto acetals

[Tiecco, M.; Testaferri, L.; Tingoli, M.; Bartoli, D. Journal of Organic Chemistry, 1990 , vol. 55, # 15 p. 4523 - 4528]

More Articles...