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Preparation of Stable Diacyl Orthoester by O‐Insertion on Reaction of a 1,2‐Diketone with Lead Tetraacetate
Author(s) -
Mohr Siegfried
Publication year - 1981
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198106891
Subject(s) - orthoester , chemistry , degradation (telecommunications) , diketone , stereochemistry , organic chemistry , telecommunications , computer science
Not the expected spirocyclic triketone but the diacyl orthoester (2) is formed on oxidative degradation of the amino acid function in (1) with Pb(OAc) 4 . The unusual stability of the orthoester is possibly due to the spatially overcrowded structure, evidenced by X‐ray structure analysis.