A Convenient Method for the Synthesis of Terminal (E)-1,3-Dienes ..
A tetracyclic anhydride, synthesized and well described by Reppe (best-known under the name of Reppe-Anhydride) turned out to be the ideal compound for our purpose 15 (Figure ). It is easily available by the classic Diels-Alder-Reaction of cyclooctatetraene (COT) 13 and maleic anhydride 14. [-] Additionally to the anhydride function this tetracyclic compound possesses a reactive double bond inside of the cyclobutene ring. The presence of a further double bond inside of the cyclohexene ring is not of relevance due to the inactivity of this double bond in the DARinv. The anhydride ring of the tetracyclic compound can be converted to the substituted corresponding imides, whereas the yield is nearly quantitative and the product can be purified easily by recrystallization (scheme/table ). Further ring systems, dedicated for chemical reactions as described above, are the cyclobutene-3,4-dicarboxylic acid anhydride [, ], as well as the commercially available and norbornen-anhydrides.
A general method for the synthesis of 1,3-dienes
Synthesis of Highly Substituted Symmetrical 1,3-Dienes via ..
Indium-Mediated 1,2,4,5-Hexatetraen-3-ylation of 4-Acetoxy-2-azetidinones and Their Applications to the Diels-Alder Reactions for the Synthesis of 2-Azetidinone Derivatives, 2008,
for the Differential Vicinal Diarylation of Terminal 1,3-Dienes ..
Efficient Synthetic Method of Z-Selective2-Halo-1,3-dienes from Reactions of Allenols Possessing Ethoxycarbonyl and Vinyl Group with Indium Trihalide, 2010,