Bulletin of the Chemical Society of Japan p. 2977 - 2980 (1980)
Update date:2022-07-31
Topics:
Nakamura, Mikio
Oki, Michinori
A series of 10,10-disubstituted 9-(2,6-xylyl)-9,10-dihydroanthracene derivatives have been prepared and their conformations and barriers to internal rotation about the Cxylyl-C9 bond have been examined.These compounds exist predominantly as a pseudo-equatorial form in the ground state for rotation.A large effect is inserted by the substituents in 10 position on barriers to rotation and is interpreted in terms of a rotation-inversion mechanism rather than a simple rotation mechanism for the methyl-exchange process which is observed by 1H NMR spectra.The highestbarrier to rotation has been found in the compound having two peri-chloro groups and a hydroxyl group in 9-position.The high barrier is ascribed to destabilization of the transition state, where 9-aryl group takes axial conformation, due to the three electronegative groups which are forced to be arranged parallelly in quite a near region.The change of 9-OH to 9-H thus decreases the barrier to rotation when peri-chlorines are present, while the increase in barrier is observed as in the case of 9-aryfluorenes and 9-arylxanthenes when they are absent.
View MoreXinjiang Fufeng Biotechnologies Co., Ltd.
Contact:+86-539-7287111
Address:GANQUANPU INDUSTRIAL PARK, ECONOMIC AND TECHNOLOGICAL DEVELOPMENT AREA (TOUTUNHE DISTRICT) OF URUMQI
Contact:+86-518-81061113
Address:No. 8 Lingzhou Road, Lianyungang, Jiangsu, China
Chongqing Werlchem Fine Chemical Co. Ltd
Contact:+86-23-67521957
Address:NO.15,Fortune Road,Yubei District,401121,Chongqing,China
Jinan Decheng Hemu Medical Technology Co.,Ltd.
Contact:+86-531-68650525
Address:NO.554 Zhengfeng Road High-new Technology Development Zone
Contact:0027-717-456976
Address:2ND FLOOR, 325 VAUSE ROAD, OVERPORT, 4001, SOUTH AFRICA
Doi:10.1016/S0040-4039(01)85854-8
(1978)Doi:10.1016/j.tet.2004.02.065
(2004)Doi:10.1055/s-2000-6254
(2000)Doi:10.1246/bcsj.52.1441
(1979)Doi:10.1016/j.tetlet.2005.01.089
(2005)Doi:10.1055/s-2005-865319
(2005)