Issue 4, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

N-(3-Cyanoprop-2-ynyl)carbazole: synthesis, crystal structure, and solid-state reactivity

Ulf Drechsler,a   Daniel J. Sandmana  and  Bruce M. Foxmanb  

a Center for Advanced Materials, Department of Chemistry, University of Massachusetts Lowell, Lowell, Massachusetts, USA

b Department of Chemistry, Mail Stop 015, Brandeis University, Waltham, Massachusetts, USA

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.

Graphical abstract: N-(3-Cyanoprop-2-ynyl)carbazole: synthesis, crystal structure, and solid-state reactivity

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Article information

DOI
https://doi.org/10.1039/B007807G
Article type
Paper
Submitted
26 Sep 2000
Accepted
24 Jan 2001
First published
27 Feb 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 581-584

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N-(3-Cyanoprop-2-ynyl)carbazole: synthesis, crystal structure, and solid-state reactivity

U. Drechsler, D. J. Sandman and B. M. Foxman, J. Chem. Soc., Perkin Trans. 2, 2001, 581 DOI: 10.1039/B007807G

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