Journal of the American Chemical Society p. 3943 - 3949 (1993)
Update date:2022-08-03
Topics:
Maruoka, Keiji
Concepcion, Arnel B.
Murase, Noriaki
Oishi, Masataka
Hirayama, Naoki
Yamamoto, Hisashi
Reactive aldehydes such as formaldehyde and α-chloro aldehydes can be successfully generated by treatment of readily available trioxane and α-chloro aldehyde trimers, respectively, with methylaluminum bis(2,6-diphenylphenoxide) (MAPH), and stabilized as their 1:1 coordination complexes with MAPH. The resulting CH2=O·MAPH complex reacts with a variety of olefins to furnish ene-reaction products with excellent regio- and stereoselectivities. In addition, this complex as well as α-chloro aldehyde-M APH complexes can be utilized as a stable source of gaseous formaldehyde and reactive α-chloro aldehydes, respectively, for the nucleophilic addition of various carbanions (organometallics, enolates, etc.). Formation of reactive aldehyde-MAPH complexes is firmly confirmed by 1H NMR spectroscopy. A space-filling model of aldehyde-M APH complexes implies that formaldehyde and α-chloro aldehydes coordinated with MAPH may be electronically stabilized by two parallel phenyl groups of aluminum ligands.
View MoreShandong Topscience Biotech Co., Ltd.
Contact:0633-2619278
Address:No. 98 Lanshan West Road, Lanshan District, Rizhao, Shandong Province, P.R. of China
Daqing E-shine Chemical Co.,LTD
Contact:0086-024-31285112
Address:Hongweiyuan area, Ranghulu district
Shijiazhuang Frontierchem Co., Ltd.
Contact:+86-311-89271196
Address:4-4-202 No.15 Biandian Street,Shijiazhuang
jintan yufan Medicine Raw materials Co.,Ltd.
Contact:86-519-82808282
Address:6th,Jincheng Huangzhuang
Contact:+86-18653358619
Address:zibo
Doi:10.1016/S0040-4039(00)77603-9
(1993)Doi:10.1016/S0040-4039(00)60435-5
(1993)Doi:10.1135/cccc19930649
(1993)Doi:10.1021/jo01256a072
(1969)Doi:10.1080/00397919308009822
(1993)Doi:10.1016/j.tetlet.2013.10.032
(2013)