Phenoxyacetic acid dianion

R3B - RCHzCOOH. Phenoxyacetic acid forms a dianion (2) by treatment with 2equiv.of LDA inTHF at 0°. The dianion reacts with trialkylboranes to form an... 

B-alkyl-9-BBN derivatives (p. 1077). Since only the 9-alkyl group migrates, this method permits the conversion in high yield of an alkene to a primary alcohol or aldehyde containing one more carbon." When B-alkyl-9-BBN derivatives are treated with CO and lithium tri-ferf-butoxyaluminum hydride," other functional groups (e.g., CN and ester) can be present in the alkyl group without being reduced." Boranes can be directly converted to carboxylic acids by reaction with the dianion of phenoxyacetic acid." " ... 

The electrochemical reaction of organoboranes in the presence of propenoic acid esters has been reported to be a convenient synthesis of carboxylic esters while with acetone, trialkylboranes react electrochemically to yield dioxaboro-lanes (6) and dioxaborinanes (7) [reaction (3)]. The first direct synthesis of carboxylic acids from organoboranes has been published and involved the reaction of trialkylboranes and the dianion of phenoxyacetic acid in THF [reaction (4)]. ... 

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