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Volumn , Issue 12, 2007, Pages 1887-1889

An efficient and inexpensive multigram synthesis of 3,4-dibromo- and 3,4-dichlorofuran-2(5H)-one

Author keywords

Furan 2(5H) ones; Polyfunctional compounds; Reduction; Regioselectivity; Sodium borohydride

Indexed keywords

MUCOBROMIC ACID; MUCOCHLORIC ACID; MULTIGRAM SYNTHESIS; POLYFUNCTIONAL COMPOUNDS;

EID: 34347392335     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-965964     Document Type: Article
Times cited : (21)

References (30)
  • 1
    • 34347382950 scopus 로고    scopus 로고
    • For the regioselective and stereospecific synthesis of alkyl 3-aryl-, 3-alkyl- and 3-alk-1-ynyl-substituted (Z)-2-bromopropenoates by palladium-catalyzed cross-coupling reactions involving alkyl (Z)-2,3-dibromopropenoates, see: (a) Rossi, R.; Bellina, F.; Carpita, A. Recent Res. Dev. Synth. Org. Chem. 1998, 1, 47.
    • For the regioselective and stereospecific synthesis of alkyl 3-aryl-, 3-alkyl- and 3-alk-1-ynyl-substituted (Z)-2-bromopropenoates by palladium-catalyzed cross-coupling reactions involving alkyl (Z)-2,3-dibromopropenoates, see: (a) Rossi, R.; Bellina, F.; Carpita, A. Recent Res. Dev. Synth. Org. Chem. 1998, 1, 47.
  • 13
    • 50849151376 scopus 로고    scopus 로고
    • sp2 halides, see: (a) Fitton, P.; Rick, E. A. J. Organomet. Chem. 1971, 28, 287.
    • sp2 halides, see: (a) Fitton, P.; Rick, E. A. J. Organomet. Chem. 1971, 28, 287.
  • 27
    • 0027962458 scopus 로고    scopus 로고
    • Mucobromic acid (14a) and mucochloric acid (14b) exhibit bacterial mutagenicity in the Salmonella typhimurium (TA100-S9) assay, and their mean molar mutagenicities are 5.54 and 2.92 revertant/mmol, respectively. However, 3,4-dibromofuran-2(5H)-one(1a) and 3,4-dichlorofuran-2(5H)-one (1b) are consistently less mutagenic than 14a and 14b: LaLonde, R. T.; Leo, H. R. Chem. Res. Toxicol. 1994, 7, 779.
    • Mucobromic acid (14a) and mucochloric acid (14b) exhibit bacterial mutagenicity in the Salmonella typhimurium (TA100-S9) assay, and their mean molar mutagenicities are 5.54 and 2.92 revertant/mmol, respectively. However, 3,4-dibromofuran-2(5H)-one(1a) and 3,4-dichlorofuran-2(5H)-one (1b) are consistently less mutagenic than 14a and 14b: LaLonde, R. T.; Leo, H. R. Chem. Res. Toxicol. 1994, 7, 779.
  • 28
    • 0029011141 scopus 로고    scopus 로고
    • Mucochloric acid (14b) is formed during chlorine disinfection of drinking water: (a) Jansson, K.; Hyttinen, J. M.; Mittykoski, M.; Maki-Paakkanen, J. Environ. Mol. Mutag. 1995, 25, 284.
    • Mucochloric acid (14b) is formed during chlorine disinfection of drinking water: (a) Jansson, K.; Hyttinen, J. M.; Mittykoski, M.; Maki-Paakkanen, J. Environ. Mol. Mutag. 1995, 25, 284.
  • 29
    • 34347394537 scopus 로고    scopus 로고
    • Mucochloric acid (14b) also originates from chlorination in soft wood pulping: (b) Holmbom, B. R.; Voss, R. H.; Mortimer, R. D.; Wong, A. Environ. Sci. Technol. 1994, 18, 333.
    • Mucochloric acid (14b) also originates from chlorination in soft wood pulping: (b) Holmbom, B. R.; Voss, R. H.; Mortimer, R. D.; Wong, A. Environ. Sci. Technol. 1994, 18, 333.
  • 30
    • 34347398258 scopus 로고    scopus 로고
    • Reaction times longer than 15 min produced crude reaction mixtures which were contaminated by 5-20% of 3-bromofuran-2(5H)-one.
    • Reaction times longer than 15 min produced crude reaction mixtures which were contaminated by 5-20% of 3-bromofuran-2(5H)-one.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.