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Wanzlick‐Carbene in der [4 + 1]‐Cycloaddition mit Bis(methylthio)‐ und Bis(trifluormethyl)‐1,2,4,5‐tetrazin
Author(s) -
Frenzen Gerlinde,
Kümmell Andreas,
MeyerDulheuer Christiane,
Seitz Gunther
Publication year - 1994
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.19941270933
Subject(s) - chemistry , cycloaddition , carbene , tetrazine , intramolecular force , nucleophile , electrophile , medicinal chemistry , stereochemistry , trifluoromethyl , organic chemistry , catalysis , alkyl
Wanzlick Carbenes in the [4 + 1] Cycloaddition Reaction with Bis(methylthio)‐ and Bis(trifluoromethyl)‐1,2,4,5‐tetrazine The 3,6‐disubstituted 1,2,4,5‐tetrazines 3 and 4 have been submitted to a [4 + 1] cycloaddition reaction with the nucleophilic singlet carbenes (Wanzlick carbenes) 2a–d , which are generated from the precursors 1a–d . With 3 as diazadiene the expected spiro compounds 6a–d are formed. In contrast to this presumed two‐step reaction sequence of 3 , with the tetrazine 4 the cascade cycloaddition/cycloelimination is surprisingly followed by an intramolecular electrophilic aromatic substitution to yield the chiral tetracyclic compounds of type 8 with high diastereoselectivity. The crystal structure of 8d has been determined by X‐ray diffraction methods.