By Norbert De Kimpe, Roland Verhe(auth.)
An up to date treatise on heteroallylic halides (?-haloketones, ?-haloaldehydes, and ?-haloimines). provides fresh learn effects pertaining to availability of the name compounds, their chemical homes and reactivity towards chosen carbon, nitrogen, oxygen, and sulfur nucleophiles, and their function in sleek natural synthesis.
Chapter 1 Synthesis and reactivity of ??halogenated ketones (pages 1–119):
Chapter 1 Appendix to bankruptcy 1: Synthesis and reactivity of ??halogenated ketones (pages 121–223):
Chapter 2 ??Halogenated imines (pages 225–277):
Chapter 2 Appendix to bankruptcy 2: ??Halogenated imines (pages 279–368):
Chapter three Synthesis and reactivity of ??halogenated aldehydes (pages 369–449):
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Additional resources for α-Haloketones, α-Haloaldehydes and α-Haloimines
Monobromination occurs smoothly and geminal dibromination rarely takes place, so that brominated ketones which are not available by the bromine method can be synthesized. However, the reaction rate is much slower with N-bromo compounds and in some cases no bromination occurs at allzo6. 209. Bromination of isophorone (124) with NBS gives rise to 4-bromoisophorone (136) (equation 84)202. g. N-bromophthalimide, N-bromoacetamide, N-bromotolylsulphonylamide, 3-bromo- and 1,3-dibromo-5,5-dimethylhydantoin have been used less frequently as brominating agents2".
The diactivated epoxides are then opened at both sides to produce the final isomeric apdialkoxy ketones 245 and 246 (equation 137). ^^. The intermediacy of a-chloro-a'-methoxyoxiranes seems to be reasonable as compounds of this type have been observed during the reaction of tetrachlorocyclopentanone (38) which gives 248 and 249 (equation 1 3 8 ) v In addition, stable a-chloro-a'-methoxy oxiranes (251) have been isolated during the reaction of tetrachlorocyclohexanones (250) with sodium methoxide in methanol (equation 139)332.
The initially formed a-hydroxyketones sometimes undergo further reactions under the basic reaction conditions, such as i s o m e r i z a t i ~ n ~oxidation ~~, with formation of diketones2w, benzylic rearrangement with formation of a-hydroxycarboxylic acids291and d i m e r i z a t i ~ n ~ ~ ~ . Numerous examples are known of Favorskii rearrangements of a-halogenated ketones with metal hydroxide~2~3, carbonates294,bicarbonates295and silver nitrate296 in water, as depicted below (equation 112). In some cases, such as polyhalogenated cycloalkanones, even treatment with water gives rise to Favorskii products293.