Allyl halides hydrogenolysis

Hydrogenation of C=C, C=NOH, C=N. Ham and Coker found rhodium-alumina the catalyst of choice for hydrogenation of vinylic and allylic halides with minimal hydrogenolysis, for example ... 

Alkylation of metal chelates of sucrose with allyl halides and sodium bromo-acetate in DMSO yielded mono-O-allylated and mono-O-carboxymethylated derivatives. A new acidic monosaccharide from the O-specific lipopolysaccharide of Shigella dysenteriae type 3 has been identified as 4-0-[(/ )-l-carboxy-ethyl]-D-glucopyranose on the basis of chemical and mass-spectral evidence and by its synthesis by alkylation of methyl 2,3,6-tri-0-benzyl-a(P)-D-glucopyranoside with (5)-2-chloropropionic acid, esterification (with diazomethane), hydrogenolysis, and acid hydrolysis. ... 

Water-soluble transition-metal complexes have been used recently for transfer hydrogenolysis of halocarbons. Paetzold and Oehme [110] have realized the reductive dehaiogenation of allyl or benzyl halides in the presence of [(phosphine) 2PdCl2] complexes with sulfonated phosphines as ligands (e.g., Ph2P(CH2)3S03K) by... 

This chapter surveys the reduction of saturated alkyl halides to alkanes. Reductive -eliminations of vicinal dihalides to alkenes are also described briefly. Reduction of vinyl and aryl halides is covered in this volume. Chapter 4.5 hydrogenolysis of allyl and benzyl halides is covered in this volume. Chapter 4.7, and reduction of a-halo-substituted carbonyl compounds CX—CO to carbonyl compounds CH—CO is covered in this volume. Chapter 4.8. 

Hydrogenolysis of Allyl and Benzyl Halides and Related Compounds... 

Hydrogenolysis of allylic compounds was rather general, including halides, acetates, alcohols, ethers and amines. 

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