Please use this identifier to cite or link to this item: https://doi.org/10.1016/S0040-4039(97)00399-7
Title: Restriction of the inversion process of the 1,3-bridged ring of the rigid conformer of 24-methyl-2,17-dithia[3.3](2,2')biphenyleno(1,3)cyclophane
Authors: Lai, Y.-H. 
Ang, S.-G. 
Wong, S.-Y. 
Issue Date: 7-Apr-1997
Citation: Lai, Y.-H., Ang, S.-G., Wong, S.-Y. (1997-04-07). Restriction of the inversion process of the 1,3-bridged ring of the rigid conformer of 24-methyl-2,17-dithia[3.3](2,2')biphenyleno(1,3)cyclophane. Tetrahedron Letters 38 (14) : 2553-2556. ScholarBank@NUS Repository. https://doi.org/10.1016/S0040-4039(97)00399-7
Abstract: The title compound 3 was prepared via a cyclization reaction between two known precursors. It is confirmed that the inversion process of the 1,3-bridged ring in the 2,17-dithia[3.3](2,2')biphenyleno(1,3)cyclophane system was restricted with a conformational energy barrier of >84 kJ mol-1. The adopted rigid conformation is represented by 3a (or 3b) having the methyl protons located above the cavity of one of the benzene rings. This is consistent with the preferred conformation derived from semiempirical molecular orbital PM3 calculations. All the protons in this rigid conformer could be assigned by its COSY spectra and results from a series of NOE experiments.
Source Title: Tetrahedron Letters
URI: http://scholarbank.nus.edu.sg/handle/10635/94719
ISSN: 00404039
DOI: 10.1016/S0040-4039(97)00399-7
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