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Synthesis, resolution and rates of racemisation of 1-(2′-methyl-3′-indenyl)-2-naphthylamine and -2-naphthol

✍ Scribed by Robert W. Baker; James A. Taylor

Book ID
108379785
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
109 KB
Volume
41
Category
Article
ISSN
0040-4039

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Asymmetric synthesis of axially chiral 1
Asymmetric synthesis of axially chiral 1-(2′-methyl-3′-indenyl)naphthalenes via prototropic rearrangements of stable rotamers of 1-(2′-methyl-1′-indenyl)naphthalenes
✍ Robert W. Baker; Joost N.H. Reek; Brian J. Wallace 📂 Article 📅 1998 🏛 Elsevier Science 🌐 French ⚖ 280 KB

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 °C leads to the formation of an 18:1 mixture of -ac:+sc-6 rotamers, with a barrie