- A new approach to the synthesis of (Z)-2-fluoro-2-alkenals via Wittig-type carbonyl condensation reactions of 2-(fluoromethyl)-4,4,6-trimethyl-1,3-oxazine phosphonium bromide
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We report here the transformation of aldehydes to their (Z)-α-fluoro-α,β-unsaturated aldehyde homologs by condensation with the phosphonium salt of the Meyer's oxazine obtained from bromofluoroacetonitrile. After methylation with trimethyloxonium tetrafluoroborate the quaternized oxazine is cleanly reduced to mostly Z 2-fluoro-2-alkenals by sodium borohydride at room temperature. This methodology is compatible with usual protecting groups and affords an efficient access to functionalized mostly Z 2-fluoro-2-alkenals derived from natural products and their corresponding (Z)-2-fluoro-2-alkenols.
- Kajjout, Mohammed,Smietana, Micha?l,Leroy, Jacques,Rolando, Christian
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p. 1658 - 1660
(2013/03/29)
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- Synthetic Studies for Novel Structure of α-Nitrogenously Functionalized α-Fluorocarboxylic Acids. Part 1. The First Synthesis and Reactions of N-Protected α-Fluoroglycines
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The first synthesis of the N-protected α-fluoro-α-amino acid esters 12, 13, 21 and 22, and the corresponding acids 16 and 24, is described.Reaction of ethyl and t-butyl bromofluoroacetates 4 and 9 with di-t-butyl and dibenzyl iminodicarboxylate potassium
- Takeuchi, Yoshio,Nabetani, Manabu,Takagi, Kumiko,Hagi, Toru,Koizumi, Toru
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- 2-Fluoro-2-cyanoethenyl cyclopropane carboxylates as pesticides
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Novel cyclopropanecarboxylates in all possible isomeric forms or mixtures thereof of the formula STR1 with a 1R,cis or 1R,trans structure and wherein X is a halogen, R is selected from the group consisting of (A) optionally unsaturated alkyl of 2 to 12 ca
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- Halonitriles, their preparation and use to make halopyridines
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Novel halonitriles, e.g., 2,4-dichloro-2-fluoro-5,5-dimethoxy-4-methylpentanenitrile, method of preparation and use to make halopyridines, some of which are novel, e.g., 2-chloro-3-fluoro-5-methylpyridine. These compounds are intermediates in the preparation of pharmaceutical and agricultural products.
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