Stereospecific 1,4-Addition of Organolithium Reagents to Unprotected 1- and 2-Naphthalenecarboxylic Acids. A Facile Route to 1,1,2- and -1,2,2-Trisubstituted 1,2-Dihydronaphthalenes

Radiosynthesis of a 2‐substituted 4,5‐dihydro‐1H‐[2‐11C] imidazole: the I2 imidazoline receptor ligand [11C] benazoline

“…8), we did not further explore this option, the more so because there would be a risk of attack of non-reacted n-butyllithium on the naphthalene system of the formed 2-[ 11 C]naphthoic acid. 9 For the second step, the conversion of 2- 1 -cartridge procedure. It was eluted from the cartridge with a small amount of ethanol followed by physiological serum or citric acid buffer (pH=4.7), the latter giving a slightly better result.…”

Intermolecular Dearomatising Addition of Organolithium Compounds to N-Benzoylamides of 2,2,6,6-Tetramethylpiperidine

“…Naphthalenes may similarly undergo nucleophilic attack by organolithium compounds,12 though dearomatisation of a naphthalene rings requires additional activation in the form of an electron‐withdrawing substituent 13. Naphthalenecarboxamides,14 naphthalenecarboxylic acids15 and their esters,16,17 naphthalenimines,18,19 and most importantly naphthyloxazolines20−23 all accept nucleophiles, losing aromaticity in one ring and providing valuable synthetic intermediates.…”

Cyclisations of Organolithiums onto Aromatic Rings

“…Nucleophilic addition of organolithiums to naphthalene rings with rearomatisation has been known for some time, and Stoyanovich, 65 Meyers 66,67 and others [68][69][70][71] have shown how to use electron-withdrawing groups to stabilise the addition products and hence give dihydronaphthalenes, many of them of synthetic use. We aimed to develop an intramolecular version of this reaction, allowing annelation of a five membered ring, for example, to a naphthalene system.…”