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In Tabellen werden unter Auswertung von zahlreichen Lit.‐ Stellen nucleophile Substitutionsreaktionen mit Boranat beschrieben, die z.B. zur Umwandlung von Halogeniden oder Sulfonaten (I) in Kohlenwasserstoffe, zur Eliminierung einer Methylgruppe aus den aus (IV) hergestellten Ammonium‐Verbindungen (V) zu den tert. Aminen (VI) oder auch zu einer Spaltung von Disulfonylimiden (VII) unter Bildung der Kohlenwasserstoffe (VIII) führen können.

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The reductions of a variety of conjugated aldehydes and ketones with NaBHaCN in acidic methanol and hexamethylphosphortriamide (HMPT) have been investigated. Alicyclic carbonyl compounds afforded principally the corresponding allylic alcohols in both solvents with methyl ethers as side products in methanol. The introduction of additional conjugation often resulted in reduction to allylic hydrocarbons, presumably via acid-induced ionization and hydride trapping. Formation of saturated alcohols was not observed in any alicyclic cases studied. Cyclic enones, on the other hand, gave mixtures of allylic and saturated alcohols resulting from competing 1,2 and 1,4 addition of cyanoborohydride.

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