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Volumn 133, Issue 15, 2011, Pages 5913-5920

Radical chain reduction of alkylboron compounds with catechols

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL RADICALS; C-C BOND FORMATION; CATECHOL DERIVATIVES; CHAIN REACTION; HIGH TEMPERATURE; HYDROGEN ATOMS; HYDROGEN TRANSFER; ORDER OF MAGNITUDE; ORGANOBORON; PHENOXYL RADICAL; PROTONOLYSIS; RADICAL CHAIN; RADICAL INHIBITOR; REACTION CONDITIONS; SIMPLE REACTION; TIN HYDRIDES;

EID: 79954507577     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja110224d     Document Type: Article
Times cited : (68)

References (70)
  • 24
    • 79954556638 scopus 로고    scopus 로고
    • To avoid the undesired reduction of the B -alkylcatecholboranes, we recommend quenching the excess catecholborane with tert -butanol instead of methanol
    • To avoid the undesired reduction of the B -alkylcatecholboranes, we recommend quenching the excess catecholborane with tert -butanol instead of methanol.
  • 36
    • 79954563701 scopus 로고    scopus 로고
    • 4- tert -Butylcatechol (Aldrich catalog number 124249, as of October 2010) costs $73.50 for 500 g and has a LD50 of 2 g/kg.
    • 4- tert -Butylcatechol (Aldrich catalog number 124249, as of October 2010) costs $73.50 for 500 g and has a LD50 of 2 g/kg.
  • 39
    • 79954518500 scopus 로고    scopus 로고
    • The corresponding alcohols never exceeded 2% of the product, and generally only traces can be observed in GC MS analysis.
    • The corresponding alcohols never exceeded 2% of the product, and generally only traces can be observed in GC MS analysis.
  • 42
    • 0038337738 scopus 로고    scopus 로고
    • Other radical processes involving B -alkylcatecholboranes generated in situ by a rhodium catalyzed hydroboration have been reported, see
    • Other radical processes involving B -alkylcatecholboranes generated in situ by a rhodium catalyzed hydroboration have been reported, see: Renaud, P.; Ollivier, C.; Weber, V. J. Org. Chem. 2003, 68, 5769-5772
    • (2003) J. Org. Chem. , vol.68 , pp. 5769-5772
    • Renaud, P.1    Ollivier, C.2    Weber, V.3
  • 47
    • 79954453475 scopus 로고    scopus 로고
    • 11B NMR: δ = 56.99 ppm) that was attributed to diethyl catecholborinic ester 7.
    • 11B NMR: δ = 56.99 ppm) that was attributed to diethyl catecholborinic ester 7.
  • 48
    • 79954568008 scopus 로고    scopus 로고
    • Reaction with atmospheric oxygen often prevents clean thin layer chromatography analysis. Moreover, boron derivatives were found highly detrimental to our GC columns and samples had to be filtered over aluminium oxide prior to chromatography. Thus, only the disappearance of the starting alkene and the formation of the reduced product can be monitored.
    • Reaction with atmospheric oxygen often prevents clean thin layer chromatography analysis. Moreover, boron derivatives were found highly detrimental to our GC columns and samples had to be filtered over aluminium oxide prior to chromatography. Thus, only the disappearance of the starting alkene and the formation of the reduced product can be monitored.
  • 62
  • 69
    • 79954505612 scopus 로고    scopus 로고
    • 2/DTBHN, or DLP always led to irreproducible results.
    • 2/DTBHN, or DLP always led to irreproducible results.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.