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Volumn 47, Issue 27, 2008, Pages 5030-5033

On the nature of the reactive intermediates in gold-catalyzed cycloisomerization reactions

Author keywords

Carbenes; Carbocations; Gold; Homogeneous catalysis; Platinum

Indexed keywords

CHEMICAL REACTIONS; CYCLIZATION; ORGANIC COMPOUNDS; STEREOSELECTIVITY;

EID: 53049098944     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800934     Document Type: Article
Times cited : (236)

References (71)
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    • The C-N bond length in 4 (1.262 Å) is even shorter than a typical RC=NR′ double bond of an imine (1.279 Å) and much shorter than a prototypical C-N single bond of an N-disubstituted amide (1.346 Å). For a useful compilation of characteristic bond lengths, see: F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor, J. Chem. Soc. Perkin Trans. 2 1987, S1-S19.
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    • Anisotropic displacement parameters are drawn at the 50% probability level and hydrogen atoms are omitted for clarity. CCDC 678991 (17), 678992 (19), and 678990 (21a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif. Short crystallographic summaries can also be found in the Supporting Information.
    • Anisotropic displacement parameters are drawn at the 50% probability level and hydrogen atoms are omitted for clarity. CCDC 678991 (17), 678992 (19), and 678990 (21a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif. Short crystallographic summaries can also be found in the Supporting Information.
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    • Only trace amounts of the regioisomeric compound, arising from attack of the alcohol at C6, were detected.
    • Only trace amounts of the regioisomeric compound, arising from attack of the alcohol at C6, were detected.
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    • Previous reactivity data thought to be supportive of gold carbenes fall into the general categories of Friedel-Crafts reactions, Prins-type processes, and cationic rearrangements, or commence with the attack of a sulfoxide see Refs, 5a-c, according to our analysis, they can be easily accounted for in cationic terms and are therefore by no means inconsistent with the views expressed in this paper
    • Previous reactivity data thought to be supportive of gold carbenes fall into the general categories of Friedel-Crafts reactions, Prins-type processes, and cationic rearrangements, or commence with the attack of a sulfoxide (see Refs. [5a-c]); according to our analysis, they can be easily accounted for in cationic terms and are therefore by no means inconsistent with the views expressed in this paper.
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    • for a theoretical study emphasizing the non-carbene character of the pertinent gold intermediates, see: O. Nieto Faza, C. Silva López, R. Alvarez, A. R. de Lera, J. Am. Chem. Soc. 2006, 128, 2434.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.