Journal of the Chemical Society. Perkin transactions II p. 497 - 506 (1988)
Update date:2022-08-05
Topics:
Eichinger, Peter C. H.
Bowie, John H.
The following systems have been studied: (i) the ion PhOC(1-)Ph2 on collisional activation undergoes Wittig rearrangement to Ph3CO(1-) before fragmentation; (ii) PhOC(1-)HCH=CH2 undergoes competing rearrangements, viz.Wittig rearrangement to Ph(CH2=CH)CHO(1-) and anionic Claisen rearrangement to (HO) deprotonated o-allylphenol, with the former reaction predominating; (iii) deprotonation of dibenzyl ether yields an unstable species wich forms PhCH2 (1-): no Wittig rearrangement is observed in the gas phase although it occurs in the condensed phase; and (iv) PhCH2OCH2CH=CH2 deprotonates to form the two interconvertible anions PhC(1-)HOCH2CH=CH2 and PhCH2OC(1-)HCH=CH2 of which the former is the more stable.Both ions give minor Wittig products, but the major process is loss of H2O to form a deprotonated dihydronaphthalene.There is some analogy between gas-phase and condensed-phase reactions in this system.The condensed-phase reaction of allyl benzyl ether under forcing conditions (lithium di-isopropylamide/tetrahydrofuran-hexamethylphosphoramide) gives the products 1-phenyl-but-3-en-1-ol, 1,2-dihydronaphthalene, and 1-(o-tolyl)prop-2-en-1-ol in the approximate ratio 4:3:1.
View MoreShanghai SMEC Trading Co., Ltd.
website:http://www.shanghaismec.com
Contact:+86-21-68811293
Address:ROOM 1101,NO.800 SHANGCHENG RD,SHANGHAI,CHINA
zhejiang huangyan wanfeng pharm chem co.ltd
Contact:+86-576- 84160728
Address:No. 5 Dazha Road, Economic,Development Zone(JiangKou), Zhejiang, China
AllyChem Co., Ltd., Dalian, China（BBChem）
Contact:+86-411-62313318/62313328
Address:No.5 of Jinbin Road, Jinzhou New District, Dalian City, Liaoning Province, P.R.China
Tianjin Dongchang Fine Chemical Industry Co., Ltd.
Contact:+86-22-29894595
Address:Economic Developing Zone, Ji County, Tianjin, China
Luoyang Aoda chemical Co.,Ltd.
Contact:+86-379-67518785 67516588
Address:MiaoWan industry district,YanShi City,Henan,China
Doi:10.1248/cpb.29.1747
(1981)Doi:10.1080/00304948.2019.1615365
(2019)Doi:10.1248/cpb.29.1951
(1981)Doi:10.1016/S0040-4039(00)00381-6
(2000)Doi:10.1021/ja045449x
(2004)Doi:10.1016/j.tetasy.2004.07.042
(2004)
