The Reduction of Phenylated Olefins with Alkali Metals in Liquid Ammonia Solution

Reactions of the Stilbene-Disodium and -Dilithium Adducts

“…Alternatively this diastereomer was prepared bjf reduction of 0.32 g. (0.001 mole) of dd,ZZ-dimethyl 3,4-diphenyladipate (10) according to the procedure described above for the weso-isomer. The crude product weighed 0.25 g., m.p.…”

“…In view of the extreme lability of these alkali metal atoms in the stilbene-disodium adduct, it is surprising that catalytic reduction does not yield 1,2-diphenylethane. However this reduction product is formed, together with sodamide, when the stilbene adduct is dissolved in liquid ammonia (10). On the other hand, Bergmann and Schlenk, and also Wooster, found that the tetraphenylethylene-disodium adduct was inert toward ammonia.…”

ALKYLBENZENES. I. SYNTHESES FROM ISOPHORONE1

“…The indene derivative was ruled out on the basis of its high refractive index (estimated nl°, 1.57 to 1.58). Of the other two, only the styrene-type hydrocarbon (l,3-dimethyl-5-n-propenylbenzene) would be expected to react with sodium in liquid ammonia (3). The high-boiling by-product was treated with sodium in liquid ammonia, reaction taking place readily, and some l,3-dimethyl-5-npropylbenzene was obtained (b.p.…”

Natrium‐ und kalium‐organische Verbindungen. Teil II: Darstellung und präparative Anwendung [1]

“…Mit der Ammonolyse des intermediaren 1.2-Dinatrium-l.ldiphenylathans konkurriert dessen Addition an nicht umgesetztes I .I-Diphenylathylen, die zu 1.4-Dinatrium-1.1.4.4tetraphenylbutan in 20 bis 30-proz. Ausbeute fiihrt [135]. Die ammoniakalische Losung fordert die Metall-Anlagerung auI3erordentlich.…”

“…So reagiert 1.1-Diphenyl-1-propen glatt, obwohl es in atherischer Losung kein Natrium-Addukt bildet [121,125c]. Ferner scheint in fliissigem Ammoniak das sonst stabile Dinatrium-tetraphenylathan durch iiberschussiges Natrium an der zentralen C-C-Bindung gespalten zu werden [135,136]:…”