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Facile Synthesis and Preferred Conformation Analysis of Cyclododeceno[b]indene
Department of Applied Chemistry, China Agricultural University, Beijing 100193, China
* Author to whom correspondence should be addressed.
Received: 23 December 2009; in revised form: 21 January 2010 / Accepted: 25 January 2010 / Published: 1 February 2010
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
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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.
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.
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.