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Volumn 12, Issue 24, 2006, Pages 6356-6365

Aluminium(III) trifluoromethanesulfonate as an efficient catalyst for the intramolecular hydroalkoxylation of unactivated olefins: Experimental and theoretical approaches

Author keywords

Aluminum; Cyclization; Lewis acids; Oxygen heterocycles; Reaction mechanisms

Indexed keywords

CYCLIZATION; LEWIS ACIDS; MARKOVNIKOV-TYPE REGIOSELECTIVITY; OXYGEN HETEROCYCLES;

EID: 33748287037     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501478     Document Type: Article
Times cited : (103)

References (52)
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    • c) J. Muzart, Tetrahedron 2005, 61, 5955-6008.
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    • All calculations were performed with AMPAC 8.16. Semichem, Inc., PO Box 1649, Shawnee, KS 66222, USA
    • All calculations were performed with AMPAC 8.16. Semichem, Inc., PO Box 1649, Shawnee, KS 66222, USA.
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    • note
    • 3-catalyzed reaction.
  • 38
    • 33748321364 scopus 로고    scopus 로고
    • note
    • +) is indeed exothermic, but we were not able to find an original reaction path leading to tetrahydrofuran 2d with a comparable or even lower activation energy than that found starting from the O complex (Table 3, entries 7 and 9). Indeed, if the reaction is to proceed, the chelate must he cleaved, and due to the relative strengths of complexation (π complexation vs O complexation), the Lewis acid remains on the oxygen atom. From these results, we propose to explain the NMR chemical shifts observed for the ethylenic carbon atoms either as resulting from the formation of this chelate B or from the C=C complex C. Both complexes can not lead to the product of the reaction, but since their formation is reversible, they can exist and therefore be observed by spectroscopy.
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    • note
    • Data compared to commercial sample.
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    • [Chem. Abstr. 1963, 60, 9784].
    • (1963) Chem. Abstr. , vol.60 , pp. 9784


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.