Boranes ethylene derivatives with

Di(isopinocampheyl)borane Resolution of racemic ethylene derivatives with optically active boranes s. 19, 720 Lithium tetrahydridoborate s. under (C2H )gN,HCl Sodium tetrahydridoborate/boron fluoride Boranes from ethylene derivatives s. 16, 753... 

Amines can be obtained under mild conditions from amides by reduction with borane and also from ethylene derivatives with borane and hydroxylamine-O-sulfonic acid or chloramine A modified Schmidt reaction gives good yields of N-subst. trifluoro-acetamides... 

Di(isopinocampheyl)borane Resolution of racemic ethylene derivatives with optically active horanes... 

Reaction of boranes with diazo compounds Synthesis of ketones from ethylene derivatives... 

Tri(cyclopentyl)borane in diglyme added at 0° to Li-n-hexylacetylide under hexane, the volatile solvent removed, methyl tosylate added at -78°, the cooling bath removed, warmed 2 hrs. at 40°, then oxidized with alkaline H2O2 -> product. Y 88%. F. e., also with other alkylating agents such as bromides, sulfates, or oxonium salts, protonation with methanesulfonic acid, and synthesis of mixtures of cis- and trans-ethylene derivs., s. A. Pelter, C. R. Harrison, and D. Kirkpatrick, Chem. Commun. 1973, 544. 

Borane-hydrogen peroxide sodium hydroxide Reaction of carbon monoxide with hydroborated ethylene derivs. 

The development 0/ the chemistry of boranes continues with outstanding results It has produced a convenient route to the less stable, terminally unsaturated compounds from the more stable, highly substituted ethylene derivatives , a facile procedure for the asymmetric synthesis of alcohols of high optical purity , and a... 

Aldehydes of different types can be conveniently prepared from the next lower halides through carbinols which are split by dia-zotized sulfanilic acid Aliphatic aldehydes in particular can be easily obtained from carboxylic acids through N-acylethylenimi-es Aldehydes, in turn, can be converted directly into nitriles with hydroxylamine hydrochloride Ketones can be efficiently prepared from ethylene derivatives via boranes and, in high purity, from labile alcohols by oxidation in an aq.-ethereal two-phase medium Heating aliphatic acids with reduced iron powder proved to be an excellent method for the prepn. of sym. straight-chain ketones /5-Aminoketones unobtainable by Mannich reaction may be prepared via halogenomagnesium enolates... 

Support-bound 1,2-diamines can be readily converted into imidazolidinones by treatment with carbonyl diimidazole [128,129]. The required diamines have been prepared on cross-linked polystyrene by reduction of peptides bound to MBHA resin with borane. Similarly, bicyclic imidazolines have been prepared from triamines and thiocarbonyl diimidazole (Entry 10, Table 14.3). Dehydration of polystyrene-bound monoacyl ethylene-1,2-diamines yields 4,5-dihydroimidazoles (cyclic amidines, Entry 5, Table 13.18). Several groups have reported the synthesis of 2-aminoimidazol-4-ones from resin-bound amino acid derivatives (e.g., Entry 6, Table 15.11). Most of these compounds are, however, unstable, and slowly decompose if dissolved in DMSO (Jesper Lau, private communication). 

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