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C–O Insertion Reaction of Nucleophilic Carbene: Facile Synthesis of Isochromane Cage
Author(s) -
Poliakov Dmytro,
Shevchenko Igor
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200601130
Subject(s) - chemistry , carbene , intramolecular force , azetidine , phthalic anhydride , isomerization , medicinal chemistry , derivative (finance) , ring (chemistry) , nucleophile , hydrogen bond , photochemistry , stereochemistry , organic chemistry , catalysis , molecule , financial economics , economics
Bis(diisopropylamino)carbene easily reacts with phthalic anhydride to give quantitatively an isochromane derivative which undergoes unusual isomerization with the formation of a strained azetidine ring and a very short intramolecular hydrogen bond. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)