Abstract
The title compounds, 6-cyclo-propyl-1,3-diphenylfulvene, C21H18, [systematic name: 5-(cyclo-propyl-methyl-idene)-1,3-di-phen-yl-cyclo-penta-1,3-diene], 1, and 6-(2,3-di-meth-oxy-naphth-yl)-1,3-diphenylfulvene, C30H24O2, {systematic name: 5-[(3,4-di-meth-oxy-naphthalen-2-yl)methyl-idene]-1,3-di-phenyl-cyclo-penta-1,3-di-ene}, 2, were prepared from 1,3-di-phenyl-cyclo-penta-diene, pyrrolidine, and the corresponding aldehydes in an ethano-lic solution. Each structure crystallizes with one mol-ecule per asymmetric unit and exhibits the alternating short and long bond lengths typical of fulvenes. A network of C-H⋯C ring inter-actions as well as C-H⋯O inter-actions is observed, resulting in the compact packing found in each structure.
Highlights
The title compounds, 6-cyclopropyl-1,3-diphenylfulvene, C21H18, [systematic name: 5-(cyclopropylmethylidene)-1,3-diphenylcyclopenta-1,3-diene], 1, and 6(2,3-dimethoxynaphthyl)-1,3-diphenylfulvene, C30H24O2, {systematic name: 5[(3,4-dimethoxynaphthalen-2-yl)methylidene]-1,3-diphenylcyclopenta-1,3-diene}, 2, were prepared from 1,3-diphenylcyclopentadiene, pyrrolidine, and the corresponding aldehydes in an ethanolic solution
As a continuation of our work in this area, we report the crystal structures of 6-cyclopropyl-1,3diphenylfulvene, 1, and 6-(2,3-dimethoxynaphthyl)-1,3diphenylfulvene, 2
Fulvene 1 packs side by side along the a-axis direction with molecules oriented in such a way that the 6-cyclopropyl groups are sandwiched between the 1-Ph and 3-Ph rings of adjacent fulvene molecules
Summary
Pentafulvenes are a unique class of cross-conjugated organic molecules commonly synthesized using aldehyde and cyclopentadiene starting materials under a variety of conditions (Thiele, 1900; Stone & Little, 1984; Sieverding et al, 2019). 1,3,6-trisubstituted fulvenes have been used as starting materials in the synthesis of bridged cyclopentadiene ligands and ansa-Ln complexes (Adas & Balaich, 2018). 2. Structural commentary Compounds 1 (Fig. 1) and 2 (Fig. 2) crystallize in the orthorhombic space groups Pbca and P212121, respectively. Structural commentary Compounds 1 (Fig. 1) and 2 (Fig. 2) crystallize in the orthorhombic space groups Pbca and P212121, respectively Both fulvenes crystallize with one molecule per asymmetric unit (Z0 = 1), exhibit the expected alternating short–long bond lengths within the fulvene core and display very similar bond lengths
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