Journal of the Chemical Society. Perkin transactions I p. 2937 - 2943 (1996)
Update date:2022-08-02
Topics:
Mueller, Dirk
Boehme, Marc
Nieger, Martin
Rissanen, Kari
Voegtle, Fritz
A series of helical-chiral 1-thia-10-aza[2.2]metacyclophanes 2-11 with different substituents at the nitrogen atom and at the aromatic ring have been synthesised and their chiroptical properties examined. These new N-substituted phanes are more suitable for the investigation of structure-chiroptics relationships than the already characterised N-tosylated aza[2.2]phanes. Their absolute configuration can be derived by comparison with the known parent compound 1 with free NH in the bridge. Chiral separations were achieved by HPLC, using a cellulose carbamate-coated, chiral column material. The secondary amine 1 has been derivatised at the nitrogen atom with various electrophiles. The X-ray structures of 1-4 give detailed information about deformation and distortion in the [2.2]metacyclophane skeleton. In the N-tosyl[2.2]metacyclophanes 8-11, containing stilbene chromophores, the UV absorption is shifted bathochromically. The disturbing influence of the tosyl chromophore in the CD spectra can be accounted for by the separation of the stilbene transitions. The synthetic method used is demonstrated to be more generally applicable to strained secondary amines by preparing the first chiral and even more strained thiaza[2.2]orthometacyclophane 15. Copyright 1996 by the Royal Society of Chemistry.
View Morewebsite:http://www.arromax.com
Contact:+86-0512-62959601 skype:aimmezhang
Address:Suite 401, Bldg A3, 218 Xinghu St.Suzhou Industrial Park 215123, P.R. China
Suqian Ruixing Chemical Co., Ltd.
Contact:+86-527-80805666（总机）;84836008(销售)
Address:3 Jingsilu, Zone north, Hubin Xincheng Development Park, Suqian, China
Beijing Wisdom Chemicals Co., Ltd.
Contact:+86-10-52350335
Address:F2, BLDG 19, Liando Valley U, Majuqiao, Tongzhou District, Beijing, China
Nantong LiKai Chemical Co.,Ltd
Contact:+86-513-89068669
Address:Jincheng Science Park
Tianjin Derchemist Sci-Tech Co., Ltd.
website:http://www.derchemist.com
Contact:+86-22-58627059
Address:Xinmao Science and Technology Park，Huayuan Industrial Park
Doi:10.1021/jacs.5b06077
(2015)Doi:10.1002/chem.201302526
(2013)Doi:10.1021/ja501093m
(2014)Doi:10.1021/ja500699x
(2014)Doi:10.1002/ejoc.201301481
(2014)Doi:10.1021/jo00097a049
(1994)
