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Thiourea: A Novel Cleaving Agent for 1,3-Dioxolanes

IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata

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Title Thiourea: A Novel Cleaving Agent for 1,3-Dioxolanes
Creator Majumdar, Swapan
Bhattacharjya, Anup
Subject Chemistry
Description One of the most common methods of protecting aldehydes, ketones, and vicinal diols involves the formation of acetals. Aldehydes and ketones are usually protected as their 1,3-dioxolane derivatives, and vicinal diols such as those present in carbohydrate derivatives are protected as 2,2-dimethyl-1,3-dioxolanes. Several methods are available for deprotecting these types of acetals, which mostly utilize acidic cleaving methods.1 Other cleaving methods involving the use of silica gel2 or lithium tetrafluoroborate in wet acetonitrile3 and some nonaqueous cleaving methods have also been reported for this purpose.4-6 Herein we report that thiourea can effect the cleavage of 1,3-dioxolanes derived from aldehydes and ketones, as well as the selective cleavage of the 5,6-O-isopropylidene moiety in 1,2:5,6-di-O-isopropylidene hexose derivatives, leading to good to excellent yields of the parent compounds.
Publisher American Chemical Society
Date 1999
Type Article
Format application/pdf
Identifier http://www.eprints.iicb.res.in/698/1/JOURNAL_OF_ORGANIC_CHEMISTRY__64_(15_)5682%2D5685_;1999[36].pdf
Majumdar, Swapan and Bhattacharjya, Anup (1999) Thiourea: A Novel Cleaving Agent for 1,3-Dioxolanes. The Journal of Organic Chemistry, 64 (15). pp. 5682-5685.
Relation http://dx.doi.org/10.1021/jo981115c