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Hydrolysis of Difluorocyclopropenes: the Role of the Cyclopropenyl Cation and the Effects of Substituents

Year: 2025

Type: article

Abstract: Monosubstituted gem-difluorocyclopropenes undergo hydrolysis yielding cyclopropenones and acrylic acid derivatives. Herein, we investigate the reaction routes of hydrolysis for both aromatic and alkyl derivatives. The study supports the idea that the formation of a cyclopropenyl cation controls the reactivity of gem-difluorocyclopropenes, and aromatic substituents accelerate the hydrolysis via the resonance stabilization. Reaction conditions, including the solvent composition and temperature, significantly affect the conversion and the product selectivity. This information facilitates the preparative synthesis and improves understanding of the fluorinated cyclopropene reactivity.

Source: Journal of organic and pharmaceutical chemistry

DOI: 10.24959/ophcj.25.324913

Authors: Mykola O. Pashko, Serhiy V. Ryabukhin

Institutions: Taras Shevchenko National University of Kyiv, Enamine (Ukraine), National Academy of Sciences of Ukraine, Institute of Organic Chemistry

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: diamond

Funder: Ministry of Education and Science of Ukraine

OpenAlex ID: W4410696448

FWCI: 0.347

Cites: 9

Cited by: 1

Related to: 10