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A direct entry to a semibullvalene structure by an abnormal diels-alder reaction. Mass spectrometry evidence of highly stable non-benzenoid aromatic cyclooctatetraene dications.

✍ Scribed by F. Serratosa; P. Solá


Book ID
104246719
Publisher
Elsevier Science
Year
1973
Tongue
French
Weight
188 KB
Volume
14
Category
Article
ISSN
0040-4039

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✦ Synopsis


Pursuing

our studies on the synthesis of acetylene diethers e benzyne intermediates', we prepared 1,2,3,4_tetramethoxynaphthelene (I)+ (white crystals, m.p. 55-56nC; n.m,r. in OCC13, Z 1.6-2.6 (m, AS system)(4H), 5.92 (s)(6H) and 5.95 (s)(6H); Found: C, 67.63;H, 6.41) which was then condensed with tetrechlorobenryne (II), generated in situ from hexaohloroben---2 zene , end the reaction mixture chromatografed on alumina: two isomeric adducts ware lsolated in 7.5 and 1.3% yield, together with 35.8% of recovered tetramethoxynaphthalene I.