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1,3‐Diethoxy‐2‐azaindenylium‐hexachloroantimonat – ein destabilisiertes, cyclisches 1,3‐Dialkoxy‐2‐azaallyl‐Kation
Author(s) -
Funke Wolfgang,
Würthwein ErnstUlrich
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250826
Subject(s) - chemistry , ring (chemistry) , moiety , antiaromaticity , salt (chemistry) , regioselectivity , medicinal chemistry , alkylation , diradical , sodium salt , oxygen atom , stereochemistry , aromaticity , organic chemistry , molecule , catalysis , inorganic chemistry , physics , nuclear physics , singlet state , excited state
1,3‐Diethoxy‐2‐azaindenylium Hexachloroantimonate – a Destabilized, Cyclic 1,3‐Dialkoxy‐2‐azaallyl Cation Regioselective alkylation at the carbonyl oxygen atom of 3‐ethoxyisoindolenone ( 3 ) by using a triethyloxonium salt yields the title salt 4 , a new anti‐Hückel‐aromatic compound. The isomeric N ‐acyliminium salt 5 is not observed. 13 C‐ and 14 N‐NMR‐spectroscopic methods indicate unusual charge distribution in the five‐membered ring of 4 ; on the basis of AM1 calculations, this is attributed to ring strain exerted on the 2‐azaallyl moiety. Antiaromatic π‐interactions in this formally 8π‐electron system are minimized by lengthening of the benzylic bonds, as indicated by AM1 data.