Journal of Organometallic Chemistry p. 17 - 27 (1972)
Update date:2022-08-02
Topics:
Goasdoue, Nicole
Gaudemar, Marcel
Organozinc compounds derived from α-bromonitriles are readily prepared in solution in tetrahydrofuran (THF) and exist in the C metallated form. They condense normally with aldehydes and saturated ketones. A number of new β-hydroxy-nitriles are described. The addition of conjugated unsaturated ketones results in the formation of β-hydroxynitriles or ketonitriles, depending on the nature of the initial bromonitrile. The stereochemistry of the reaction of benzaldehyde with zinc-α-bromonitrile is not influenced by the nature of the solvent. Condensation with diethyl-malonate alkylidenes lead to the expected 1,4-addition products.
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Doi:10.1021/ja0010960
(2000)Doi:10.1248/cpb.49.1352
(2001)Doi:10.1016/S0022-328X(00)81831-8
(1972)Doi:10.3762/bjoc.15.275
(2019)Doi:10.1055/s-0036-1588635
(2017)Doi:10.1016/S0040-4039(01)84567-6
(1972)
