Stereochemistry of the Hydroboration of Alkenes

George Kabalka, Ray J. Newton, John Jacobus

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

The reactions of (E)-and (Z)-l-hexene-1, 2-d2 with dialkylboranes (dicyclohexylborane and 9-BBN) produce threo-and erythro-(1, 2-dideuteriohexyl)dialkylboranes, respectively. Further, the reactions of (E)-and (Z)-l-hex-ene-2-d1 with di(2-deuteriocyclohexyl)borane-B-d1 produce erythro-and thereo-(l, 2-dideuteriohexyl)di(deuterio-cyclohexyl)borane, respectively. These results constitute direct evidence that the hydroboration reaction involves the cis addition of the boron hydrogen moiety to the alkene.

Original languageEnglish (US)
Pages (from-to)1567-1569
Number of pages3
JournalJournal of Organic Chemistry
Volume43
Issue number8
DOIs
StatePublished - Jan 1 1978
Externally publishedYes

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Boranes
Stereochemistry
Alkenes
Boron
Hydrogen
1-hexene

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Stereochemistry of the Hydroboration of Alkenes. / Kabalka, George; Newton, Ray J.; Jacobus, John.

In: Journal of Organic Chemistry, Vol. 43, No. 8, 01.01.1978, p. 1567-1569.

Research output: Contribution to journalArticle

Kabalka, George ; Newton, Ray J. ; Jacobus, John. / Stereochemistry of the Hydroboration of Alkenes. In: Journal of Organic Chemistry. 1978 ; Vol. 43, No. 8. pp. 1567-1569.
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