Reducing characteristics of borohydride exchange resin-CuSO 4 in methanol

Taebo Sim, Nung Min Yoon

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Reducing characteristics of borohydride exchange resin (BER)-CuSO 4 (cat.) were studied in methanol at room temperature. Carbon-carbon double bonds conjugated with benzene or carbonyl group were more rapidly reduced than was the case with isolated double bonds. Carbonyl groups were readily reduced, whereas esters and amides were inert, and nitriles were slowly reduced. High chemoselectivity was also observed in halide reductions: p-bromochlorobenzene and p-bromoiodobenzene were reduced quantitatively to chlorobenzene and bromobenzene, respectively. Aliphatic epoxides were inert to this reagent; however, styrene oxide derivatives were readily reduced to the corresponding deoxygenated products. Aliphatic azides were reduced slowly during 6 h, whereas phenyl azide was transformed to aniline in 1 h. Nitrocyclohexane was reduced at room temperature, but nitrobenzene, nitrosobenzene, azobenzene, and azoxybenzene required an elevated temperature (65 °C) for rapid reductions (1 h). Similarly, N,N-dimethylanihne N-oxide was reduced at room temperature, whereas pyridine N-oxide required refluxing. Finally, among the sulfur compounds tested, only diphenyl disulfide was reduced readily, and sulfide, aliphatic disulfide, sulfoxide, sulfone, and tosylate were inert to this reducing system.

Original languageEnglish
Pages (from-to)1101-1107
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume70
Issue number5
DOIs
Publication statusPublished - 1997 Dec 1
Externally publishedYes

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Borohydrides
Methanol
Resins
sulfoxide
styrene oxide
Azides
Carbon
Sulfur Compounds
Temperature
Nitriles
Sulfones
Epoxy Compounds
Sulfides
Benzene
Amides
Disulfides
Oxides
Esters
Derivatives

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Reducing characteristics of borohydride exchange resin-CuSO 4 in methanol. / Sim, Taebo; Yoon, Nung Min.

In: Bulletin of the Chemical Society of Japan, Vol. 70, No. 5, 01.12.1997, p. 1101-1107.

Research output: Contribution to journalArticle

Sim, Taebo ; Yoon, Nung Min. / Reducing characteristics of borohydride exchange resin-CuSO 4 in methanol. In: Bulletin of the Chemical Society of Japan. 1997 ; Vol. 70, No. 5. pp. 1101-1107.
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