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Unexpected synthesis of 2-methyl 1,3-diazapyrene from 1,8-diamino naphthalene

✍ Scribed by A. Edel; P.A. Marnot; J.P. Sauvage

Publisher
Elsevier Science
Year
1985
Tongue
French
Weight
111 KB
Volume
26
Category
Article
ISSN
0040-4039

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✦ Synopsis

Treatment of 1,8-diamino naphthalene by glycerol, under Skraup conditions, leads to 2-methyl 1,3-diazapyrene and not to quinoC7,8-hlquinoline. Aromatic polyimines are widely used in coordination chemistry because of the accessibility of their first 'I[* orbitals, once bound to transition metals'. Surprisingly, the

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Reaction of methyl (R)-l-(p-tolylsulfinyl)naphthalene-2-carboxylate 2 with 2-methylindenyllithium affords the -ac rotamer of methyl (S)-l-(2'-methyl-l'-indenyl)naphthalene-2-carboxylate 6 in 63% ee. Heating -ac-6 at 80 Β°C leads to the formation of an 18:1 mixture of -ac:+sc-6 rotamers, with a barrie