Journal of the Chemical Society. Perkin transactions I p. 1047 - 1054 (1990)
Update date:2022-08-04
Topics:
Kennedy, Michael
McKervey, M. Anthony
Maguire, Anita R.
Tuladhar, Sarbajna M.
Twohig, M. Fiona
Rhodium(II) acetate-catalysed cyclisation of α-diazoketones derived from 3-arylpropionic acid produces bicyclo<5.3.0>decatrienones or 2-tetralones depending on the substitution pattern of the aryl ring in the precursor; the former products are transformed into the latter catalytically with trifluoroacetic acid.Precursors with methyl, methoxy, and acetoxy substituents have been examined, efficient cyclisation occurring in all cases.When the precursor contains a meta-methoxy substituent, 2-tetralones are obtained directly.The efficient conversion of 3-phenylpropionicacid into trans-1-methylbicyclo<5.3.0>decan-2-one is also described, partial asymmetric synthesis having been realised through the use of rhodium (S)-mandelate as the cyclisation catalyst.Cyclisations of diazoketones derived from 4-phenylbutyric acid and 5-phenylpentanoic acid have also been studied; the former provides a new entry into the bicyclo<5.4.0>undecane system whereas the latter produces a 2,3-disubstituted cyclopentanone via C-H insertion.Aspects of the cycloheptatriene-norcaradiene equilibrium in fused ring systems are discussed.
View MoreShanghai Yuanding Chem. Sci. & Tech. Co., Ltd.
website:http://www.shydtec.com
Contact:86-21-57721279
Address:Science and Technology Park, Songjiang District, Shanghai, China
Luzhou North Chemical Co., Ltd.
Contact:+86-830-2796784；+86-830-2796776
Address:Gaoba, Longmatan District, Luzhou, Sichuan Province
Yantai Derun Liquid Crystal Materials Co. Ltd.
website:http://www.ytderun.com
Contact:86-535-6300169
Address:ROOM 90, XIANGFU STREET, FUSHAN NEW-HIGH-TECH IDUSTRY ZONE, YANTAI
Chengdu Alfa Biotechnology Co.,Ltd.
website:http://www.alfabiotech.com/
Contact:86-28-85142057
Address:No.230,Longyin Road,Xipu,Pixian County
Beijing Greenchem Technology Co.,Ltd. ( Panjin Greenchem Technology Co.Ltd .)
website:http://www.bjgreenchem.com/
Contact:+86-427-6515887
Address:301,302, 3rd Floor, Building C-7, Dongsheng Science Park, Northern Territory, Zhongguancun, No. 66, Xixiaokou Road, Haidian District, Beijing
Doi:10.1021/jm049924d
(2004)Doi:10.1016/S0040-4039(01)95014-2
(1978)Doi:10.1016/j.tetlet.2004.02.117
(2004)Doi:10.1007/s10870-016-0640-4
(2016)Doi:10.1016/0040-4020(78)87007-0
(1978)Doi:10.1016/j.ica.2003.11.026
(2004)
