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Synthesis 2017; 49(15): 3357-3365
DOI: 10.1055/s-0036-1588458
DOI: 10.1055/s-0036-1588458
short review
Recent Advances in Cyclic Diacyl Peroxides: Reactivity and Selectivity Enhancement Brought by the Cyclic Structure
Financial support was granted by the ‘Hundred Talents Program’ of the Harbin Institute of Technology (HIT), the ‘Fundamental Research Funds for the Central University’ (HIT.BRETIV.201502), the NSFC (21202027), the NCET (NCET-12-0145), the Open Project Program of Hubei Key Laboratory of Drug Synthesis and Optimization, Jingchu University of Technology (no. opp2015ZD01), and the ‘Technology Foundation for Selected Overseas Chinese Scholar’ of the Ministry of Human Resources and Social Security of China (MOHRSS).Further Information
Publication History
Received: 28 April 2017
Accepted after revision: 22 May 2017
Publication Date:
12 June 2017 (online)
Dedicated to Professor Herbert Mayr on the occasion of his 70th birthday
Abstract
Preliminarily studies on cyclic diacyl peroxides have shown novel and superior reactivities compared with their acyclic diacyl peroxide counterparts in many reaction types. After summarizing the methods available for the preparation of cyclic diacyl peroxides and describing their structural features, this review brings together an overview of their reactivities with respect to oxidations and decarboxylations, and demonstrates the advantages of reactions with cyclic diacyl peroxides, which include metal-free, additive-free, milder conditions, higher yields and better selectivities.
1 Introduction
2 Methods of Preparation of Cyclic Diacyl Peroxides
3 Structures and Stabilities of Cyclic Diacyl Peroxides
4 Oxidation Reactions
4.1 Oxidative Additions to Alkenes
4.2 Oxidation Reactions of Heteroatoms
4.3 Oxidation Reactions of 1,3-Dicarbonyl Compounds
4.4 Hydroxylations of Arenes
5 Decarboxylations
6 Conclusion
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