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Iron‐Mediated Conversions of Eucarvone‐Derived Cationic Dienyl Complexes
Author(s) -
Hirschfelder Andreas,
Drost Daniel,
Meinhardt Sven,
Eilbracht Peter
Publication year - 1996
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.19961290718
Subject(s) - chemistry , cationic polymerization , nucleophile , regioselectivity , moiety , substituent , diene , medicinal chemistry , ring (chemistry) , stereochemistry , nucleophilic substitution , substitution reaction , alkoxy group , organic chemistry , catalysis , natural rubber , alkyl
Cationic cycloheptadienyl iron complexes with new substitution patterns are generated by starting from the eucarvone complex 5 and the analogous triphenyl phosphite complex 6 . These complexes are converted with different nucleophiles. Regioselectivity of the nucleophilic attack depends on the substitution pattern of the seven‐membered ring. A new type of cationic system 7b , bearing an alkoxy substituent at C‐1, was treated with nucleophiles leading to the ipso adducts of type 10 . Unexpected attack at the central C‐3 of the dienyl moiety is observed during the conversion of cationic complexes of type 9 with nucleophiles. The diene iron complexes, obtained in these reactions, can be converted to substituted cycloheptadienes by oxidative decomplexation, as shown by a selected example.