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An efficient protection of carbonyls and deprotection of acetals using decaborane

โœ Scribed by Seung Hwan Lee; Ji Hee Lee; Cheol Min Yoon


Book ID
104250810
Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
350 KB
Volume
43
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


Carbonyls were efficiently converted to the corresponding dimethyl acetals at room temperature using trimethyl orthoformate and 1 mol% of decaborane under a nitrogen atmosphere. In turn, acetals were deprotected to the corresponding carbonyls using 1 mol% of decaborane in aqueous THF chemoselectively.


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A novel type of photodeprotection reaction of simple aromatic acetals and ketals is described. The deprotection is highly efficient under optimized conditions. The aromatic ring confers the photoreactivity to the compounds. The efficiency of the process depends on the structure of the acetal moiety.