Related Experiment Video
Updated: Oct 25, 2026

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
Insertion into Donor-Acceptor Cyclopropanes with Carbon-Sulfur Moieties Derived from Sulfoxonium Ylides and Elemental
Vu H Luu1,2, Dat H Tran1,2, Tien V Le1,2
1VNU-HCM Key Laboratory of Advanced Materials and Structures, Ho Chi Minh City University of Technology (HCMUT), Ho Chi Minh City84, Vietnam.
Abstract:
The (3 + 2) cycloaddition of donor-acceptor cyclopropanes (DACs) with carbon-sulfur 2π components has become an emerging method to rapidly assemble tetrahydrothiophenes. Starting materials donating the carbon-sulfur unit are often isolated from thionation of carbonyls or carboxylic acid derivatives. Herein we report a method for the cycloaddition of DACs with carbon-sulfur moieties presumably formed in situ via β-sulfuration of α-carbonyl sulfoxonium ylides with elemental sulfur. The insertion occurred without the assistance of Lewis acid, perhaps due to the strongly polarized carbon-sulfur-containing intermediate. The hitherto challenging α-monosubstituted tetrahydrothiophenes were obtained with a wide range of tolerated functionalities.
Related Concept Videos
Preparation and Reactions of Sulfides
Preparation and Reactions of Thiols
Electrophilic Aromatic Substitution: Sulfonation of Benzene
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Cycloaddition Reactions: Overview
Cycloaddition Reactions: MO Requirements for Thermal Activation
