Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/95084
Title: Synthesis and rigid conformers of 14,15-dimethyl-2,11-dithia[3.3]-(1,3)(1, 4)cyclophane and 12,13-dimethyl[2.2](1,3)(1,4)cyclophane
Authors: Lai, Y.-H. 
Yap, A.H.-T.
Issue Date: 1993
Citation: Lai, Y.-H.,Yap, A.H.-T. (1993). Synthesis and rigid conformers of 14,15-dimethyl-2,11-dithia[3.3]-(1,3)(1, 4)cyclophane and 12,13-dimethyl[2.2](1,3)(1,4)cyclophane. Journal of the Chemical Society, Perkin Transactions 2 (7) : 1373-1377. ScholarBank@NUS Repository.
Abstract: The dithiacyclophane 4 was synthesized from 2,3-dimethylaniline in seven steps. Only the conformer 4b was isolated. Photodesulfurization of 4b however resulted only in the isolation of the cyclophane 2a indicating an abrupt change in conformational preference going from the [3.3]phane to the [2.2]phane. Their stereochemistry could be assigned readily from the chemical shifts of the aryl protons or methyl protons on the (1,4)-bridged ring. Dynamic 1H NMR studies indicated that both 2a and 4b remained conformationally fixed up to 150°C. The conformational preference depends on the non-bonding interaction between H8 (of 2a) or H9 (of 4a) and the methyl groups and that between the (1,3)-bridged ring and the methyl groups in 2b and 4b.
Source Title: Journal of the Chemical Society, Perkin Transactions 2
URI: http://scholarbank.nus.edu.sg/handle/10635/95084
ISSN: 1472779X
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