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Jin-Oh Park, Suban K Sahoo, Heung-Jin Choi
C3v-Symmetric anion receptors 3 and 4 with urethane groups were synthesized by using trindane triol as tripodal molecular framework. In (1)H NMR titration study, the receptors showed noticeable downfield shift/disappearance of the urethane-NH peak in presence of H2PO4(-) and F(-) due to the host-guest complexation occurred through multiple hydrogen bonding and/or the deprotonation of urethane-NH groups. Other tested anions such as Cl(-), Br(-), HSO4(-), and NO3(-) showed either no or negligible chemical shift of the urethane groups...
January 15, 2016: Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
Fabrizio Fabris, Cristiano Zonta, Giuseppe Borsato, Ottorino De Lucchi
The formal annulation of three bicylic olefins yields a class of molecules termed benzocyclotrimers (BCTs), which have unusual electronic properties. The bonds in the central aromatic ring, for example, alternate in length: rather than resembling a substituted benzene, a BCT instead evokes comparison to a cyclohexatriene. Forty years have passed since the synthesis of heptiptycene, the first BCT, was reported. In the interim, many methods have been developed for preparing tris-bicycloannulated benzenes. More than thirty different BCTs have so far been reported, with a variety of morphological features and properties...
June 21, 2011: Accounts of Chemical Research
Heung-Jin Choi, Yeon Sil Park, Seok Hun Yun, Hong-Seok Kim, Chan Sik Cho, Kwangnak Ko, Kyo Han Ahn
[reaction: see text] A novel C3V-symmetric scaffold, trindane 7, has been efficiently synthesized from 1,3,5-tris(bromomethyl)-2,4,6-tris(chloromethyl)benzene (1) in six steps with 47% overall yield. The control of all-syn stereochemistry in the tribenzylation step has been achieved by blocking one side of the trindane ring as metal carbonyl complexes. The potential utility of trindane 7 as a receptor skeleton has been examined with a urea derivative 12 toward several anionic guests.
March 7, 2002: Organic Letters
S Ranganathan, K M Muraleedharan, C C Rao, M Vairamani, I L Karle
[reaction: see text] Ozonolysis of 1 largely results in 2 and 3, having features similar to several classes of natural products. The retention of the C(15) pericycle suggests preference for the cleavage of pi-bonds endo to the cyclopentane ring. This unique property of trindane offers opportunities for synthesis of complex natural products from this hydrocarbon that can be made in quantity by acid-catalyzed trimerization of cyclopentanone.
August 9, 2001: Organic Letters
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