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Volumn 7, Issue 3, 2009, Pages 553-556

Organocatalysis by bimacrocyclic NHCs: Unexpected formation of a cyclic hemiacetal instead of a γ-butyrolactone

Author keywords

[No Author keywords available]

Indexed keywords

KETONES; ORGANIC COMPOUNDS; REACTION KINETICS;

EID: 58849131488     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b815828b     Document Type: Article
Times cited : (21)

References (22)
  • 16
    • 2442420298 scopus 로고
    • In the absence of cinnamaldehyde 2a, all precatalysts (4, 5, 6a and 6b) led to very little conversion of benzaldehyde 1c, and only small amounts of benzoin 9 could be obtained Hemiacetal 7 could also be obtained when preformed benzoin 9 was reacted with cinnamaldehyde 2a in the presence of DBU Dehydrogenation also occurs when pure benzoin 9 is investigated by GC. Besides 9, benzil 8 is also detected. Respective benzoins are known to be easily oxidizable:
    • G. Bertolli G. Fronza C. Fuganti P. Grasselli L. Majori F. Spreafico Tetrahedron Lett. 1981 22 965
    • (1981) Tetrahedron Lett. , vol.22 , pp. 965
    • Bertolli, G.1    Fronza, G.2    Fuganti, C.3    Grasselli, P.4    Majori, L.5    Spreafico, F.6
  • 21
    • 33746584001 scopus 로고    scopus 로고
    • b). The 10:1 ratio between the anomers was deduced from integration Only the signals of the major anomer are listed. One quaternary aromatic carbon atom was not observed, possibly due to overlap or low intensity
    • C. Burstein S. Tschan X. Xie F. Glorius Synthesis 2006 2418
    • (2006) Synthesis , pp. 2418
    • Burstein, C.1    Tschan, S.2    Xie, X.3    Glorius, F.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.