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Light-Induced Synthesis of Tricyclic Thiolane Derivatives from 2(5H)-thiophenones via consecutive radical ring closure

✍ Scribed by René Kiesewetter; Alan Graff; Paul Margaretha

Publisher: John Wiley and Sons
Year: 1988
Tongue: German
Weight: 236 KB
Volume: 71
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19880710225

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✦ Synopsis

Two a.1 -unsaturated thiolactones, 5-(2-propynyl)-2(5H)-thiophenone (5) and 3,5-di(2-propenyl)-2(5H)-thiophenone (6), were newly synthesized. Irradiation (1 = 300 nm) of 5 in MeOH containing cyclopentene afforded a 3: 1 mixture of diastereoisomeric methyl 7-thiatricyclo[6.4.0.0z~6]dodec-10-ene-12-carboxylates (848b), while irradiation of 6 in MeOH saturated with 2-methylpropene gives a 3:2 mixture of diastereoisomeric methyl 3,3,9-trimethyl-5-thiatricyclo[6.2.1 .02*6]undecane-l-carboxylates (lOn/lOb).

') A (thermal) procedure for the preparation of 4-mercapto-2-butenoates from 2-mercaptoacetaldehyde dimer has been reported recently [5]. Results on Michael addition with such compounds had already been reported [61.

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✍ René Kiesewetter; Paul Margaretha 📂 Article 📅 1987 🏛 John Wiley and Sons 🌐 German ⚖ 208 KB

The yields indicated were determined by GC analysis and, therefore, reflect ratios of products only. 'H-NMR from 1 :1 mixture of 10 and 9. Configuration at C(5) unknown. 'H-NMR from 3:l mixture of 14 and 13. Configuration at C(2) unknown