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Naphthothiete und ihre Anwendung in der Heterocyclen-Synthese

Authors :
Axel Mayer
Herbert Meier
Norbert Rumpf
Source :
Liebigs Annalen. 1995:2221-2226
Publication Year :
1995
Publisher :
Wiley, 1995.

Abstract

Naphtothietes and Their Application to the Synthesis of Heterocycles The three isomeric naphthothietes 5, 11, and 16 were prepared according to the reaction sequences shown in Schemes 1–3. The final step was in each case a flash vacuum pyrolysis (FVP) of the corresponding mercaptonaphthalenemethanol 4, 9, and 15, respectively. The thiete rings in 5 and 11 can be opened by gentle heating; the ring opening of the isomer 16 possesses a much higher activation barrier. A MNDO calculation of the ΔHf values of 5, 11, and 16 and the open isomers 5′, 11′, and 16′ provides an explanation for the different behavior. Photochemical ring opening represents a useful alternative. The reaction Schemes 4, 6, and 7 reveal the synthetic potential of the naphtho-condensed thietes. Cycloaddition reactions with CC, CO, or CN double bonds lead into the series of differently condensed thiopyrans 17, 18, 24, 25, 26, 3,1-oxathiine 19 and 1,3-thiazines 20, 21.

Details

ISSN :
10990690 and 09473440
Volume :
1995
Database :
OpenAIRE
Journal :
Liebigs Annalen
Accession number :
edsair.doi...........5bc1a72307dcb89c77688283a427d92f
Full Text :
https://doi.org/10.1002/jlac.1995199512308