N-(3-Cyanoprop-2-ynyl)carbazole: synthesis, crystal structure, and solid-state reactivity
- 27 February 2001
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 4,p. 581-584
- https://doi.org/10.1039/b007807g
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.Keywords
This publication has 0 references indexed in Scilit: