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The reaction of several terpene 1,3-dienes with 4-methyl-1,2,4-triazoline-3,5-dione

✍ Scribed by Roland Rienäcker; Pnina Ashkenazi; Moshe Kapon; Reinhard Benn; David Ginsburg

Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
379 KB
Volume
43
Category
Article
ISSN
0040-4020

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✦ Synopsis

Several 1,3-dienic terpenes of various structural types are attacked by the title dienophile from the less hindered side. The regiospecificity of attack by methyl triazolinedione(MTAD), 1, upon 1,3-conjugated dienes belonging to the [2.2.2Jbicyclooctane or the norbornane families has been shown to occur mainly from the more hindered side and explained by means of secondary interaction within the o-7 frame. ' In view of the work of Gleiter, Paquette et al we studied .a system containing the a-pinene skeleton and found the absence of any such interactions, i.e. nopadiene reacts with MTAD and PTAD from the lea8 hindered side.2 We now report results of other 1,3-dienic terpenes which all indicate that here too Diels-Alder attack occurs from the less hindered side. These are accompanied, in some cases, by products of the -ene reaction.

Seven terpenio substrates were investigated but results are reported for five of them 2-b.

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✍ Gary W. Breton 📂 Article 📅 2011 🏛 Elsevier Science 🌐 French ⚖ 329 KB

The reaction of 4-methyl-1,2,4-triazoline-3,5-dione (MeTAD) with substituted benzenes under the influence of trifluoroacetic acid catalysis was investigated. Generally, good-to-high yields of 1-arylurazoles resulting from aromatic substitution were obtained. Successful reaction required moderately e