Peter A. A. Klusener

Regiospecific Functionalization of Dimetalated (1-Naphthyl)acetylene. Efficient Synthetic Procedures for Naphtho[2,1-b]chalcophenes

Abstract Treatment of (1-naphthyl)acetylene (1) with two mol equivalents of the BuLi-t-BuOK reagent in tetrahydrofuran/hexane, followed by successive addition of anhydrous lithium bromide, sulfur, selenium, or tellurium and t-butylalcohol gives naphtho[2,1-b]thiophene, -selenophene and -tellurophene in good yields. Reaction of dimetalated 1 with iodine or dimethyldisulfide afforded 2-iodo-, and 2-thiomethyl(1-ethylnyl)naphthalene.

A Practical Large-Scale Synthesis of (1-Naphthyl)acetylene

Abstract 1-Ethynylnaphthalene has been synthesized on a large scale with high overall yields starting from 1-bromonaphthalene.

Direct metallation of isoprene

Treatment of isoprene with an excess of the couple potassium t-butoxide–lithium tetramethylpiperidide in tetrahydrofuran, followed by addition of a higher alkyl bromide or oxirane, gives the dienes H2CCHC(CH2)CH2R (R = alkyl or –CH2CH2OH) in reasonable yields.