Sequential treatment of 2,3-dichloropropene with magnesium and n-BuLi generated the equivalent of 1,3-dilithiopropyne, which adds regiospecifically to aldehydes and ketones to produce homopropargyl alcohols. The lithium acetylide intermediate formed in this protocol can be further reacted with aromatic and vinyl halides, under palladium catalysis, to produce 4-substituted homopropargyl alcohols and 5-en-3-yn-1-ols, respectively, in one-pot with good overall yields.

Several aromatic homopropargyl alcohols, and derivatives were prepared by one-pot reaction of 1,3-dilithiopropyne (or its equivalent) with aldehydes and ketones. The antibacterial activity, of alcohols thus prepared, against Gram (+) and Gram (−) bacteria was tested. This activity varies depending upon substitution on the homopropargyl alcohol unit. Apparently, the benzene ring and the free hydroxyl group (or its alcoxide) are needed, in the homopropargyl alcohol unit, to be biologically active.

The asymmetric unit of the title homopropargyl alcohol, C20H16OS, contains two independent molecules comprising a hydroxy group, a 3-(2-thiophenyl)propargylic moiety and two aromatic rings linked to a central carbon atom. The two unique molecules are linked into a dimer by an O—H...O hydrogen bond. In one molecule, the thiophene ring is disordered over two orientations rotated by 180° with a refined occupancy ratio of 0.575 (4):0.425 (4). The crystal structure is stabilized by O—H...π and C—H...π hydrogen-bond interactions. The crystal studied was a two-component non-merohedral twin, the refined ratio of the twin components being 0.575 (4):0.425 (4).

In the title compound, C17H16O2, the central carbon atom has a distorted tetrahedral geometry [spread of angles = 105.71 (8)–112.75 (9)°] for its bonds to a homopropargylic but-2-yn-1-ol moiety, a hydroxy group and two phenyl substituents. In the crystal, O—H...O hydrogen-bonding interactions link the molecules into [001] chains and C—H...π(ring) contacts consolidate the packing.

The asymmetric unit of the title compound, C16H14O, contains one molecule with a central carbon atom having a distorted tetrahedral geometry made of a propargylic fragment, a hydroxy group and two aromatic rings. Directional interactions such as unusual O—H...π contacts are observed between the molecules in the crystal.