Concerning Aromatic Acetylenic Carbinols

Abstract

Numerous aldehydes and ketones have been combined successfully with sodium acetylide under varying conditions to form acetylenic carbinols. Of the aromatic aldehydes reported2•3 benzaldehyde was the only aromatic aldehyde that gave a good yield of its corresponding acetylenic carbinol.

New Synthesis of Furans: the Rhodium‐Catalysed Carbonylative Addition of Arylboronic Acids to Propargylic Alcohols/ Cyclisation Sequence

“…1-(p-Chlorophenyl)-2-propyn-1-ol was synthesised according to a reported procedure by reaction between sodium acetylide and benzaldehyde. [14] Propargyl alcohol was distilled from CaH 2 prior to use, the other propargylic alcohols were used without further purification. [Rh(CO) 2 I] 2 was synthesised according to a reported method.…”

Reactions of Organic and Organometallic Compounds with Solutions of Metals in Liquid Ammonia.

“…by carbonation of alkali acetylides with carbon dioxide either in liquid ammonia or in inert hydrocarbon solvents (201,291,449). These and other applications (35,145,163,166,169,170,172,173,181,182,183,194,197,210,211,269,301,302,336,347) serve to illustrate the scope of application of these reagents. Sodium acetylide exhibits but little reactivity toward acetals (231), and sodium and potassium acetylides fail to metálate 1-heptyne to any appreciable extent (141), while both amyl-and phenyl-acetylene are partially metalated.…”