Solid State Deprotection of Acetals and Thioacetals Using Benzyltriphenylphosphonium Peroxymonosulfate 英文参考文献.docVIP

Molecules 2002, 7, 674-680 molecules ISSN 1420-3049 Solid State Deprotection of Acetals and Thioacetals Using Benzyltriphenylphosphonium Peroxymonosulfate Abdol Reza Hajipour*,1, Shadpour E. Mallakpour1 , Iraj Mohammadpoor-Baltork2 and Hadi Adibi1 1 Pharmaceutical Research Laboratory, College of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran, Fax: +98-311-3912350. 2 Department of Chemistry, Isfahan University, Isfahan 81744, Iran. *Author to whom correspondence should be addressed; e-mail: haji@cc.iut.ac.ir Received: 17 January 2002; in revised form: 18 August 2002/ Accepted: 21 August 2002 / Published: 31 August 2002 Abstract: A variety of acetals and thioacetals 2 are deprotected to the corresponding parent carbonyl compounds 3 under solvent-free conditions using benzyltriphenyl- phosphonium peroxymonosulfate (1) in the presence of aluminum chloride. Keywords: Acetals; Benzyltriphenylphosphonium peroxymonosulfate; Carbonyl compounds; Thioacetals; Solvent-free deprotection. Introduction Carbonyl compounds are often protected as thioacetals in organic synthesis [1], particularly in multistep natural product synthesis [2], due to their stability in both acidic and basic conditions. Many procedures are available in the literature for preparing thioacetals [3], but their deprotection to the parent carbonyl compounds is not always an easy process. Therefore, various hydrolytic [4] or oxidative methods [5] have been documented in recent years for dethioacetalization of thioacetals. Recently, the use of manganese-based oxidants (KMnO4, BaMnO4 and MnO2) in aprotic solvents for selective deprotection of thioacetals has been reported [6]. Carbonyl derivatives such as acetals and  Molecules 2002, 7 675 ketals are also of importance for the characterization and purification of carbonyl compounds [1], and extensive studies on the deprotection of these deriva