Electrophile induced rearrangement of 1-alkynylaluminium ate complexes

Tetrahedron Letters

Volumn 40, Issue 32, 1999, Pages 5943-5944

  Debuigne, Antoine ^a   Gérard, Julien ^a   Hevesi, Làszlò ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

Author keywords

Alkynylaluminium; Ate complex; Rearrangement; Vinylaluminium; Vinylsulfide

Indexed keywords

UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLALUMINUM;

ARTICLE; CHEMICAL REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033529918     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01179-X     Document Type: Article

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18. 1H NMR spectrum with that of the same compound obtained via similar rearrangement of the analogous boron ate complex, see ref. 9. It is worth noting that the Z stereoisomer was not present in the crude product mixture; we assume that it originates from the prolonged contact with silica gel during purification.
19. The strongly suspected presence (on the basis of GC/MS scrutiny) of the internal alkynes 6 in most product mixtures is in favor of this interpretation; however, the sometimes uncorrelated relative amounts of 6 and 8 indicate that it isn't entirely satisfactory.