Mesoions and ketene valence isomers. Three types of rearrangement of mesoionic pyridopyrimidinylium olates involving ketene intermediates

A Fiksdahl, C Plüg, C Wentrup

Index: Fiksdahl, Anne; Plueg, Carsten; Wentrup, Curt Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 9 p. 1841 - 1845

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Citation Number: 28

Abstract

The ketene valence isomers of mesoionic pyrimidinylium olates undergo (i) a retro-ene type fragmentation to C 3 O 2 16 and 2-aminopyridine 15,(ii) an electrocyclisation to form a naphthyridine (19→ 20→ 21), or (iii) a cycloreversion to 2-pyridyl isocyanate 26 and a ketene 25.

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