ISSN:
0009-2940
Keywords:
Singlet carbenes
;
[4 + 1] Cycloadditions
;
1,2,4,5-Tetrazines
;
SEAr reactions, intramolecular
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Wanzlick Carbenes in the [4 + 1] Cycloaddition Reaction with Bis(methylthio)- and Bis(trifluoromethyl)-1,2,4,5-tetrazineThe 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.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19941270933
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