Hydroxy acids Boron trichloride

A general method for the cleavage of 4,5-dihydroisoxazoles is hydrogenation over Raney nickel in the presence of an acid or a Lewis acid, such as boric acid ° or boron trichloride. The products are normally p-hydroxy ketones but in the case of compound (35), which was prepared as an intermediate in the construction of the AB-ring system of forskolin, reduction over Raney nickel gave an isolable imine (36). ... 

It is of interest to note in passing that In more recent work (ref.72), use has been made in synthesis of the transformation of chalcones to isoflavones with thallium(lll) nitrate. Thus, 6-acetyl-2,2-dimethyl-7-hydroxy-5-methoxychromanone was converted to the chalcone with 2,4-dibenzyloxybenzaldehyde. The O-acetyl derivative by treatment with the thallium reagent followed by acidic cyclisation gave a bischromanone structure. Selective reduction of the least hindered carbonyl group in the bischromanone, acidic dehydration of the resultant alcohol and final debenzylation with boron trichloride gave the linear isofiavone. 

The Inifer process developed by Kennedy can be used to functionalize vinyl monomers via a cationic route by initiating a polymerization with an alkyl halide-boron trichloride mixture R BCl. The termination by transfer to an alkyl halide leaves a halide-terminated polymer. This can be transformed to a hydroxyl terminal unit via the sequence (1) dehydrohalogenation, (2) hydroboration, and (3) oxidation and hydrolysis (Equation 5.24). These co-functional blocks may be coupled to form diblock copolymers using standard reaction techniques, e.g., diisocyanate will couple cohydroxy and co-amine blocks together. Direct reactions can also occur, and co-acid chlorides combine readily with co-hydroxy units. 

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