Intramolecular [4 + 2] cycloaddition reaction of six- and seven-membered cyclic N-allyl-C-arylethynyl iminium salts

Beitrag in einer Fachzeitschrift
(Originalarbeit)


Details zur Publikation

Autor(en): Herz HG, Schatz J, Maas G
Zeitschrift: Journal of Organic Chemistry
Verlag: American Chemical Society
Jahr der Veröffentlichung: 2001
Band: 66
Heftnummer: 9
Seitenbereich: 3176-3181
ISSN: 0022-3263


Abstract


N-Allyl-2-(het)arylethynyl-3,4,5,6-tetrahydropyridinium triflates 1c,d,e and N-allyl-2-(het)aryl-4,5,6,7-tetrahydro-3H-azepinium triflates 1g,h undergo a thermal isomerization reaction leading to derivatives of [a,f]-annulated isoindolium salts 2 in good yields. Similarly, N-allyl-2-phenylethynyl-pyridinium triflate 4 is transformed into the condensed pyridinium salt 5. An intramolecular [4 + 2] cycloaddition reaction, in which the (het)arylethynyl moiety acts as the 4π component, is considered as the key step of this transformation. In contrast, the related N-allyl-4,5-dihydro-3H-pyrrolium salts 1a,b and N-homoallyl-3,4,5,6-tetrahydropyridinium salt 1f undergo unspecific decomposition under thermal impact.



FAU-Autoren / FAU-Herausgeber

Schatz, Jürgen Prof. Dr.
Professur für Organische Chemie


Zitierweisen

APA:
Herz, H.-G., Schatz, J., & Maas, G. (2001). Intramolecular [4 + 2] cycloaddition reaction of six- and seven-membered cyclic N-allyl-C-arylethynyl iminium salts. Journal of Organic Chemistry, 66(9), 3176-3181. https://dx.doi.org/10.1021/jo015546y

MLA:
Herz, H.-G., Jürgen Schatz, and Gerhard Maas. "Intramolecular [4 + 2] cycloaddition reaction of six- and seven-membered cyclic N-allyl-C-arylethynyl iminium salts." Journal of Organic Chemistry 66.9 (2001): 3176-3181.

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