Journal of the Chemical Society. Perkin transactions II p. 1363 - 1368 (1983)
Update date:2022-08-04
Topics:
Hudson, Harry R.
Kow, Aloysius
Roberts, John C.
The reactions of neopenthyl diphenylphosphinite with chloro-, bromo-, or iodo-methane and of dineopentyl phenylphosphphonite with bromo- or iodo-methane yield crystalline alkoxyphosphonium halides.In deuteriochloroform these intermediates decompose by a first-order process which involves rate-determining collapse of the phosphonium halide ion-pair with SN2-type fission of the alkyl-oxygen bond.Rates for chloride, bromide, and iodide are similar.In a more ionising medium (deuterioacetonitrile) dissociation leads to stabilisation of the intermediates and to deviation from first-order decomposition.Previously determined X-ray diffraction data for the bromides, together with relative rates of decomposition in deuteriochloroform for intermediates in the series Phn(RO)3-nP+MeX- (n = 0,1, or 2) suggest that the stability and reactivity of alkoxyphosphonium intermediates are determined largely by inductive rather than mesomeric effects of ligands.The presence of phenoxy-substituents on phosphorus may cause a tendency towards SN1-type fission of the alkyl-oxygen bond in certain circumstances.
View MoreShijiazhuang City Xiehe Pharmaceutical Co., Ltd
Contact:+86-311-80817929
Address:Shangzhuang,Shijiazhuang,China
Contact:+86-0512-69209969
Address:Room 317,Lushan Road,Suzhou New District,Jiangsu Province,China.
website:http://www.win-winchemical.com
Contact:0086-577-64498589
Address:6F, No. 396 Xingping Road, Longwan Industrial Zone, Wenzhou City, Zhejiang, 325000 P.R.China
Contact:Tel:+86-29-88764861 Fax:+86-29-88764861
Address:Rm#2107, Block A, Epin Meidao Building, Gaoxin Rd, Hi-Tech Zone, Xi’an, China
Daqing E-shine Chemical Co.,LTD
Contact:0086-024-31285112
Address:Hongweiyuan area, Ranghulu district
Doi:10.1021/jo00323a032
(1981)Doi:10.1002/jps.2600690916
(1980)Doi:10.1021/ic50220a003
(1981)Doi:10.1021/jo00057a029
(1993)Doi:10.1016/j.apcata.2016.10.007
(2016)Doi:10.1016/S0040-4039(00)81421-5
(1983)
