28467-75-6Relevant articles and documents
Thieme Chemistry Journal Awardees - Where are they now? A general one-step synthesis of alkynes from enolisable carbonyl compounds
Lyapkalo, Ilya M.,Vogel, Michael A. K.,Boltukhina, Ekaterina V.,Vav?ík, Ji?í
scheme or table, p. 558 - 561 (2009/07/09)
Terminal and internal acetylenes were obtained in good to excellent isolated yields from carbonyl compounds by converting the carbonyl functionality into the enol nonaflate intermediate followed by elimination to give the C-C triple bond. The one-pot transformations were uniformly induced by phosphazene bases combined with mildly electrophilic nonafluorobutane-1-sulfonyl fluoride. The method is the most general among those reported to date as it applies to both acyclic ketones and aldehydes. Only moderate kinetic regioselectivity in favour of alk-1-yne achieved from methyl n-alkyl ketone represents a limitation of the method. In all the other instances, individual acetylenic products were obtained. Georg Thieme Verlag Stuttgart.
