ISSN:
0947-6539
Keywords:
cycloadditions
;
domino reactions
;
electrochemistry
;
electron transfer
;
radical ions
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Electron transfer initiated cycloaddition reactions between 2-vinylindoles, acting as heterodienes, and β-substituted enaminonitriles lead to different cycloaddition products depending on the substituents. Initiated by potentiostatically controlled electrolysis, an anellation of a cyclopropanated five-membered ring system to the diene yielding cyclopropapyrrolo[1,2-a]indoles can be achieved in just one reaction step. Interestingly, the formation of a cyclopropane ring system takes place in reaction mechanisms which involve radicals and radical cations. In addition to these products, [4 + 2]-cycloaddition products with subsequent [1,4] dialkylamino shifts can also be formed. The formation of both products can be attributed to new reaction pathways via radical cation intermediates.
Additional Material:
5 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.19970030317
Permalink
