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Volumn , Issue 22, 2010, Pages 4288-4295

Radical reduction of epoxides using a titanocene(III)/water system: Synthesis of β-deuterated alcohols and their use as internal standards in food analysis

Author keywords

Natural products; Radicals; Reduction; Titanium; Water chemistry

Indexed keywords


EID: 77954990308     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000487     Document Type: Article
Times cited : (42)

References (80)
  • 15
  • 16
    • 77955008359 scopus 로고    scopus 로고
    • 2 (99.9 atom-% D, 25 L, €221.50) are considerably more expensive
    • 2 (99.9 atom-% D, 25 L, €221.50) are considerably more expensive.
  • 17
    • 0000526264 scopus 로고
    • Some methods for the preparation of β-deuterated alcohols have been reported, leading normally to mixtures of a- and βdeuterated compounds. See: a) D. A. Evans, G. C. Fu, B. A. Anderson, J. Am. Chem. Soc. 1992, 114, 6679-6685;
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 6679-6685
    • Evans, D.A.1    Fu, G.C.2    Anderson, B.A.3
  • 39
    • 77954974427 scopus 로고    scopus 로고
    • Detailed experimental procedures and spectroscopic data for all products described in this paper can be found in the Experimental Section and Supporting Information
    • Detailed experimental procedures and spectroscopic data for all products described in this paper can be found in the Experimental Section and Supporting Information.
  • 41
    • 77954974167 scopus 로고    scopus 로고
    • 2 and Mn dust
    • 2 and Mn dust.
  • 50
    • 77954990957 scopus 로고    scopus 로고
    • The presence of trace amounts of adventitious water cannot be ruled out
    • The presence of trace amounts of adventitious water cannot be ruled out.
  • 51
    • 77954970247 scopus 로고    scopus 로고
    • 8]THF also seems to be very high and side reactions (deoxygenation reactions) become important, leading to a consequent decrease in yield. Other solvents for radical reactions, such as tτBuOMe, DMF, benzene, or trifluorotoiuene, could not be used because the in situ generation of titanocene(III) does not take place
    • 8]THF also seems to be very high and side reactions (deoxygenation reactions) become important, leading to a consequent decrease in yield. Other solvents for radical reactions, such as tτBuOMe, DMF, benzene, or trifluorotoiuene, could not be used because the in situ generation of titanocene(III) does not take place.
  • 64
    • 77954979311 scopus 로고    scopus 로고
    • 2H NMR spectroscy. Nevertheless, the diastereomeric excess was in the range of 0 to 33% de. Moreover, the stereochemical assignment could not be made unambiguously
    • 2H NMR spectroscy. Nevertheless, the diastereomeric excess was in the range of 0 to 33% de. Moreover, the stereochemical assignment could not be made unambiguously.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.