Hydrogen isotope exchange between boranes and deuterated aromatic hydrocarbons: evidence for reversible hydroboration of benzene. [Pentaborane (B/sub 5/H/sub 9/), diborane (B/sub 2/H/sub 6/)]

Journal Article · Wed Feb 13 04:00:00 EST 1985 · Inorg. Chem.; (United States)

DOI:https://doi.org/10.1021/ic00198a037· OSTI ID:5490484

Gaines, D F; Heppert, J A; Kunz, J C

Pentaborane, B/sub 5/H/sub 9/, and diborane, B/sub 2/H/sub 6/, undergo hydrogen isotope exchange with deuterated aromatic hydrocarbons. Lewis acid catalyzed hydrogen isotope exchange occurs between benzene-d/sub 6/ and the apical hydrogen atom of B/sub 5/H/sub 9/ to form 1-DB/sub 5/H/sub 8/ at ambient temperature. In uncatalyzed exchanges, B/sub 5/H/sub 9/ reacts with deuterated aromatic hydrocarbons to produce 1,2,3,4,5-D/sub 5/B/sub 5/H/sub 4/ at +45/sup 0/C and B/sub 5/D/sub 9/ at +120/sup 0/C. This thermally induced hydrogen isotope exchange apparently occurs via a reversible hydroboration of the aromatic ring. Diborane undergoes a similar isotope exchange with benzene-d/sub 6/ under mild thermal conditions. 18 references, 6 figures, 3 tables.

• Research Organization: Univ. of Wisconsin, Madison
• OSTI ID: 5490484
• Journal Information: Inorg. Chem.; (United States), Journal Name: Inorg. Chem.; (United States) Vol. 24:4; ISSN INOCA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400203* -- Isotope Exchange & Isotope Separation-- (-1987)
400303 -- Organic Chemistry-- Isotope Exchange & Isotope Separation-- (-1987)
AROMATICS
BORANES
BORON COMPOUNDS
CHEMICAL REACTIONS
DATA
DEUTERIUM
EXPERIMENTAL DATA
HYDROGEN ISOTOPES
HYDROGEN TRANSFER
INFORMATION
ISOTOPE EFFECTS
ISOTOPES
ISOTOPIC EXCHANGE
LABELLED COMPOUNDS
LABELLING
LIGHT NUCLEI
MEDIUM TEMPERATURE
NMR SPECTRA
NUCLEI
NUMERICAL DATA
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
SPECTRA
STABLE ISOTOPES
STRUCTURAL CHEMICAL ANALYSIS