Thiourea: A Novel Cleaving Agent for 1,3-Dioxolanes
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
View Archive Info| Field | Value | |
| Title |
Thiourea: A Novel Cleaving Agent for
1,3-Dioxolanes
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| Creator |
Majumdar, Swapan
Bhattacharjya, Anup |
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| Subject |
Chemistry
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| 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.
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| Publisher |
American Chemical Society
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| Date |
1999
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| 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. |
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| Relation |
http://dx.doi.org/10.1021/jo981115c
http://www.eprints.iicb.res.in/698/ |
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