Organoboranes

Buhler, Jerry D.; Brown, Herbert C.

doi:10.1016/s0022-328x(00)93364-3

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1974

1998

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Cited by 19 publications

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“…RCH2CH2Hg02CR' + B(02CR')3 (9) RCH2CH2Hg02CR' + I2 -* RCH2CH2I + IHg02CR' (10) Equations 8-10 are all well-known reactions. The presence of the boron tricarboxylate presumably formed in the mercuration step (eq 9) has been shown to be vital to the overall conversion of organomercurial to ester.…”

Section: Resultsmentioning

confidence: 99%

Mercury in organic chemistry. III. Anti-Markovnikov esterification of terminal alkenes

Larock¹

1974

J. Org. Chem.

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The direct anti-Markovnikov esterification of monosubstituted alkenes can be achieved in excellent, yields under very mild reaction conditions using a hydroboration-mercuration-iodination sequence. Hydroboration with "borane" and subsequent mercuration with a variety of mercuric carboxylates gives excellent yields of the corresponding primary alkylmercuric carboxylates. In situ iodination generates alkyl iodides which under the reaction conditions are rapidly transformed into primary esters. This procedure does not permit the synthesis of esters derived from very strong carboxylic acids or more highly substituted alkenes.

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Section: Resultsmentioning

confidence: 99%