Sign in to use this feature.

Years

Between: -

Subjects

remove_circle_outline
remove_circle_outline

Journals

Article Types

Countries / Regions

Search Results (1)

Search Parameters:
Keywords = methylenedioxolanone

Order results
Result details
Results per page
Select all
Export citation of selected articles as:
12 pages, 2310 KB  
Article
[3+2] Cycloaddition to a Chiral 5-Methylene-1,3-dioxolan-4-one and Pyrolysis of the Spiro Adducts
by R. Alan Aitken, Lynn A. Power and Alexandra M. Z. Slawin
Molecules 2025, 30(6), 1246; https://doi.org/10.3390/molecules30061246 - 10 Mar 2025
Viewed by 1250
Abstract
The [3+2] cycloaddition chemistry of (2S)-5-methylene-2-t-butyl-1,3-dioxolan-4-one, derived from lactic acid, has been examined, and spiro adducts have been obtained with benzonitrile oxide, acetonitrile oxide, diazomethane and diphenyldiazomethane. The structure and absolute stereochemistry of the benzonitrile oxide adduct has been [...] Read more.
The [3+2] cycloaddition chemistry of (2S)-5-methylene-2-t-butyl-1,3-dioxolan-4-one, derived from lactic acid, has been examined, and spiro adducts have been obtained with benzonitrile oxide, acetonitrile oxide, diazomethane and diphenyldiazomethane. The structure and absolute stereochemistry of the benzonitrile oxide adduct has been confirmed by X-ray diffraction, and all the adducts have been fully characterised by 1H and 13C NMR. Attempted cycloaddition with a nitrile sulfide, a nitrile imine and azides failed. Pyrolysis results in a range of novel gas-phase reactions, with the nitrile oxide adducts giving pivalaldehyde, CO2, the nitrile and ketene, the diazomethane adduct losing only N2 to give a cyclopropane-fused dioxolanone, and the diphenylcyclopropane derived from diphenyldiazomethane giving mainly benzophenone in a sequence involving the loss of pivalaldehyde and methyleneketene. Full article
Show Figures

Graphical abstract

Back to TopTop