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Synthesis and Structure of Heterocumulenes with and Units
Author(s) -
AlTalib Mahmoud,
Jibril Ibrahim,
Jochims Johannes C.,
Huttner Gottfried
Publication year - 1984
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.19841171107
Subject(s) - iminium , chemistry , salt (chemistry) , benzophenone , medicinal chemistry , nmr spectra database , stereochemistry , polymer chemistry , organic chemistry , spectral line , ion , physics , astronomy
Preparations, IR and NMR spectra of 1‐oxa‐3‐azabutatrienium hexachloroantimonates ( 2a – f ) and of 1‐thia‐3‐azabutatrienium hexachloroantimonate 2g are reported. According to an X ‐ray structure analysis of 2b , g these compounds crystallize as pseudocumulenes with bent C=N=C=X units ( C=N=C 129° for X = O and 139° for X = S). The extremely moisture sensitive salts 2a – e react with water to give the iminium salts 3 , while 2g gives benzophenone. With carboxylic acids the 1‐oxabutatrienium salts 2a – e afford carboxylic anhydrides (e.g. 4 ) and the iminium salts 3a – e . The α‐naphthyl compound 2c cyclizes to give the isoquinolinium salt 5 . With N , N ‐dimethylaniline 2a , e , g afford triarylcarbenium dyes ( 8 ).