Abstract
N-(3-Cyanoprop-2-ynyl)carbazole (1) was synthesized in 30% yield by reaction of N-(3-bromoprop-2-ynyl)carbazole (2) with cuprous cyanide in tetrahydrofuran, or by reaction of lithiated N-(prop-2-ynyl)carbazole (3) with 1-cyanobenzotriazole in 70% yield. Grown from hexane–dichloromethane solution, compound 1 crystallizes in the orthorhombic space group P212121, with a = 6.5553(6), b = 11.3879(25), c = 16.2752(24) Å, V = 1215.0(3) Å3, and Z = 4. The title compound undergoes a thermally induced solid-state oligomerization, largely following a 1,2-addition pathway, consistent with the arrangement of molecules observed in the crystal structure.