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Base-induced 1,4-eliminations with 3,4-dialkoxy-1, 2-alkadienes: Formation of 3-methoxy-3-alken-1-ynes

โœ Scribed by S. Hoff; B. H. Steenstra; L. Brandsma; J. F. Arens


Book ID
104587821
Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
180 KB
Volume
88
Category
Article
ISSN
0165-0513

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Hydroxy-1-phenylthio-2-alkynes (5) reacted with dihydropyran to afford the corresponding 4-tetrahydropyranyloxy derivatives which, on treatment with KHMDS, gave a mixture of (E)-and (Z)-1-phenylthio-3-alken-1-ynes, with the former predominant. When MeLi was used in the place of KHMDS, the (Z)-isomer