Abstract
The title compound, C9H7NO2, was prepared by alkynylation of 4-iodonitrobenzene with 1,3-dilithiopropyne in the presence of 1 equivalent of CuI and catalytic amounts of Pd(PPh3)2Cl2. The complete molecule is generated by crystallographic twofold symmetry with the C—N and C—C[triple-bond]C—C units lying on the rotation axis. No directional interactions beyond normal van der Waals contacts could be identified in the packing.
Highlights
The title compound, C9H7NO2, was prepared by alkynylation of 4-iodonitrobenzene with 1,3-dilithiopropyne in the presence of 1 equivalent of CuI and catalytic amounts of Pd(PPh3)2Cl2
The complete molecule is generated by crystallographic twofold symmetry with the C—N and C—C C—C units lying on the rotation axis
One of the most general methods for the synthesis of aromatic alkynes is the alkynylation of halogenated aromatic rings (Negishi & Anastasia, 2003)
Summary
One of the most general methods for the synthesis of aromatic alkynes is the alkynylation of halogenated aromatic rings (Negishi & Anastasia, 2003). The Sonogashira reaction is probably the most extensively used protocol for the synthesis of mono and disubstituted acetylenes (Sonogashira et al, 1975). In this reaction an aromatic (or vinyl) halide is treated with the corresponding acetylene, in the presence of catalytic amounts of Pd0 or PdII triphenylphosphine complexes, an amine (i.e., Et2NH) and catalytic amounts of CuI at room temperature. As part of our work in this area, we report the synthesis and crystal structure of the title compound, 1. The extended structure (Fig. 2) shows neither hydrogen bonding nor aromatic – stacking
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