en
Scientific article
English

Note on the Synthesis of 1,1-Dichloro-2,3-divinylcyclopropane and Other Functionalized Dichlorocyclopropanes

Published inHelvetica chimica acta, vol. 65, no. 4, p. 1191-1196
Publication date1982-06-16
First online date2004-10-25
Abstract

The title compound 1 was synthesized via addition of dichlorocarbene to dimethyl trars-3-hexenedioate (5), using o-nitrophenylselenic acid-elimination to form the double bonds. Reaction of dichlorocyclopropane 8 with ozone on silica gel furnished the monoketone 10; no diketone 11 could be isolated upon further exposure of 10 to O3/SiO2. When the bis(p-toluenesulfonate) 13b was treated with t-BuOK, 16 was obtained in low yield as the only isolable product. It is believed to arise from Cope-rearrangement of an intermediate cis-divinylcyclopropane 14 to cycloheptadiene 15, which undergoes a subsequent allylic rearrangement to 16.

eng
Citation (ISO format)
MULLER, Paul, REY, Michel. Note on the Synthesis of 1,1-Dichloro-2,3-divinylcyclopropane and Other Functionalized Dichlorocyclopropanes. In: Helvetica chimica acta, 1982, vol. 65, n° 4, p. 1191–1196. doi: 10.1002/hlca.19820650407
Main files (1)
Article (Published version)
accessLevelRestricted
Identifiers
ISSN of the journal0018-019X
13views
0downloads

Technical informations

Creation05/05/2023 10:48:38 AM
First validation05/05/2023 2:18:34 PM
Update time05/05/2023 2:18:34 PM
Status update05/05/2023 2:18:34 PM
Last indexation02/01/2024 10:00:36 AM
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack