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Molecules 2010, 15(2), 699-708; doi:10.3390/molecules15020699
Article

Facile Synthesis and Preferred Conformation Analysis of Cyclododeceno[b]indene

, , ,  and *
Received: 23 December 2009; in revised form: 21 January 2010 / Accepted: 25 January 2010 / Published: 1 February 2010
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Abstract: Using methanesulfonic acid as a catalyst, a series of cyclododeceno[b]indene derivatives were synthesized by the cyclization of α-benzylcyclododecanones, which were prepared by the reactions of cyclododecanones with a variety of substituted benzyl chlorides or bromides using NaH as a base. Their structures were confirmed by mp, IR spectra, 1H-NMR, 13C-NMR, MS, and x-ray diffraction. The preferred conformations were analyzed by crystal structure, 1H-NMR and quantum chemistry calculations, and compared with the x-ray diffraction structure of 2,3,5,6-bis(ortho-1,10-decylidene)dihydropyrazine. The results showed that the cyclododecene moiety adopted a preferred [1ene2333] conformation, and the substituted groups at aromatic ring had no significant influence on the conformation.
Keywords: α-benzylcyclododecanone; cyclododeceno[b]indene; synthesis; conformational analysis α-benzylcyclododecanone; cyclododeceno[b]indene; synthesis; conformational analysis
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Zhang, C.; Gong, S.; Zhang, L.; Wang, D.; Wang, M. Facile Synthesis and Preferred Conformation Analysis of Cyclododeceno[b]indene. Molecules 2010, 15, 699-708.

AMA Style

Zhang C, Gong S, Zhang L, Wang D, Wang M. Facile Synthesis and Preferred Conformation Analysis of Cyclododeceno[b]indene. Molecules. 2010; 15(2):699-708.

Chicago/Turabian Style

Zhang, Chunyan; Gong, Shengyan; Zhang, Li; Wang, Daoquan; Wang, Mingan. 2010. "Facile Synthesis and Preferred Conformation Analysis of Cyclododeceno[b]indene." Molecules 15, no. 2: 699-708.



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