Diazo reaction with boranes

Alkylation and hydrolysis of imines alkylation of aldehydes 10-107 Alkylation and hydrolysis of dithianes 10-108 Alkylation and hydrolysis of oxazines and similar compounds 10-109 Reaction of diazo aldehydes with boranes... 

Reaction of halo esters or diazo esters with boranes... 

Reaction of halo ketones or diazo ketones with boranes 10-112 Carbonylation of alkyl halides... 

Reaction of halo ketones or diazo ketones with boranes 0-102 Carbonylation of alkyl halides 0-104 Reaction between acyl halides and organometallic compounds 0-105 Reaction between other acid derivatives and organometallic compounds... 

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

Hooz reaction of boranes with diazo compds. 24,817 Huang Minion rednctimi s. Wolff-Kishner Hiinig base s. Ethyl-diisopropylamine Hydantoin ring,... 

The alkyl groups in boranes can migrate to C, too. For example, addition of the carbenoid equivalent LiCHCl2, obtained by deprotonation of CH2CI2 with LDA at low temperatures, to an alkylboronate gives the one-carbon homologous product. Other carbenoid equivalents such as diazo compounds and CO can undergo similar reactions. 

The initial intent to cover the subject exhaustively had to be abandoned because of the overwhelming amount of relevant literature. The following reactions are not covered but are briefly discussed, with references to reviews and seminal papers, in the section on Comparison with Other Methods reactions of carbanions and enolates and their surrogates with nitrogen oxides, nitrite and nitrate esters, and nitroso and nitro compounds reactions of enolates with diazonium salts, including the Japp-Klingemann reaction the diazo transfer reaction except as it interferes with the synthesis of azides the animation of boranes and the Neber rearrangement. 

In contrast to the 1,10-diaminooctahydrodecaborate itself, the perchlorinated and periodinated derivatives l,10-BioX8(NH2)l (X = Cl or I) can be bis-diazotized with sodium nitrite in mixtures of water, ethanol and acetic acid (Knoth, 1966). In the case of the reaction of l,10-BioCl8(NH2)2" Knoth obtained 14% of the mono-diazotized compound (N2)BioCl8NH3, in addition to the bis-diazo derivative (70%). No experiments are described with the aim of optimizing the mono-diazotization. Experience in the diazotization of aromatic diamines (benzene-1,4-diamine, 4,4 -diamino-l,T-diphenyl, etc., see Zollinger, 1994, Sect. 2.6) indicates that selective mono-diazotization of diamino-boranes may also be tricky. 

Similarly, a copper catalyst is thought to mediate transformation of a diazo substrate to a carbene, which inserts into P-H bonds in phosphine-boranes. When PHPh(f-Bu)(BH3) of 99% ee was used, the reaction proceeded with retention of configuration at phosphorus (Scheme 36) other chiral phosphine-boranes behaved similarly [58]. 

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