Theoretical predictions, accompanied by firm experimental verification, are presented on the "torquoselectivity" of the thermal ring opening of 3-acetylcyclobutene (1). 3-Acetylcyclobutene was synthesized from commercially available 1,1-cyclobutanedicarboxylic acid. Thermolysis of 3-acetylcyclobutene resulted in a mixture of E- and Z-dienes with a slight preference for the E-diene. This preference was reversed by the Lewis acid, ZnI(2), as predicted from theoretical calculations.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/jo951047j | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Accessing Azetidines through Magnesium-Mediated Nitrogen Group Transfer from Iminoiodinane to Donor-Acceptor Cyclopropanes.
Angew Chem Int Ed Engl
January 2025
New York University, Chemistry, 29 Washington Place, RM 10001, 10003, New York, UNITED STATES OF AMERICA.
Herein, we report a Lewis acid-mediated ring expansion of donor-acceptor cyclopropanes (DACs) to substituted azetidines via nucleophilic nitrogen group transfer from readily accessible iminoiodinane. This protocol operates under mild, transition-metal-free conditions, and showcases excellent chemoselectivity, along with broad functional group tolerance. We report for the first time that challenging alkyl donor-acceptor cyclopropanes can undergo ring expansion leading to aliphatic azetidines without relying on external oxidants or precious transition-metal catalysts.
View Article and Find Full Text PDFPolyglycidamides: from Backbone-Promoted Amidation to Degradable Polyether with Wide-Range LCST.
Angew Chem Int Ed Engl
January 2025
South China University of Technology, Faculty of Materials Science and Engineering, 381 Wushan Road, 510641, Guangzhou, CHINA.
Amide groups occur extensively in natural and synthetic polymers cultivating their vital roles in biological and industrial worlds. We report here an efficient and controlled pathway to amide-functionalized polyethers through ring-opening polymerization (ROP) of commercially available ethyl glycidate followed by amidation of the pendant ester groups. Transesterification is inhibited during the ROP by use of a two-component organocatalyst.
View Article and Find Full Text PDFAB-Type Zwitterionic Hydrogel Paint.
Langmuir
January 2025
School of Chemistry and Life Resources, Renmin University of China, 100872 Beijing, China.
Zwitterionic hydrogels exhibit excellent nonfouling and hemocompatibility. However, the practical application of these materials as antifouling coatings for biomedical devices is hindered by several key challenges, including the harsh preparation conditions and the weak coating stability. Here, we present a two-component zwitterionic hydrogel paint for the in situ preparation of robust zwitterionic hydrogel coatings on various substrate surfaces without UV assistance.
View Article and Find Full Text PDFLignin Particle Size Affects the Properties of PLA Composites Prepared by In Situ Ring-Opening Polymerization.
Polymers (Basel)
December 2024
Laboratory of Polymer and Colors Chemistry and Technology, Department of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece.
The present work focuses on the synthesis and characterization of biobased lignin-poly(lactic) acid (PLA) composites. Organosolv lignin, extracted from beechwood, was used as a filler at 0.5, 1.
View Article and Find Full Text PDFThe Network Construction of a New Byproduct-Free XLPE-Based Insulation Using a Click Chemistry-Type Reaction and a Theoretical Study of the Reaction Mechanism.
Polymers (Basel)
December 2024
Key Laboratory of Cluster Science of Ministry of Education & School of Chemistry, Beijing Institute of Technology, Beijing 100081, China.
Cross-linked polyethylene (XLPE) is applied in most advanced high-voltage direct-current (HVDC) power cable insulations, which are produced via dicumyl peroxide (DCP) technology. The electrical conductivity of insulation material can be increased by cross-linking byproducts from the DCP process. Hence, currently much attention is being paid to a new process to produce cross-linking byproduct-free XLPE.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!