Naslov
Synthesis and Reactivity Studies of 2, 4-Dimethylmethano-2, 4-didehydro-adamantane: A Comparison with Unsubstituted Analogue

Autori
Mlinarić-Majerski, Kata ; Šafar Cvitaš, Dunja ; Veljković, Jelena

Izvornik
Journal of organic chemistry (0022-3263) 59 (1994); 2374-2380

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
{; ; ; 3.1.1.}; ; ; -propellane ; dimethyl{; ; ; 3.1.1.}; ; ; -propellane ; reactivity studies

Sažetak
We prepared 2, 4-(dimethylmethano)-2, 4-didehydroadamantane (1), a gem-dimethyl{; ; ; 3.1.1.}; ; ; -propellane, and systematically examined its chemical behavior in relation to its unsubstituted analogue 2, 4-methano-2, 4-didehydroadamantane (2). 2, 4-(Dimethylmethano)-2, 4-didehydroadamantane (1) was obtained in 70% yield by pyrolysis of the dry lithium salt of the tosylhydrazone derived from 4-isopropylidene-2-adamantanone (6) in vacuo. Propellane 1 is thermally more stable than 2, but its reactivity is considerably greater than that of 2. It is highly reactive toward electrophiles and free radicals. Propellane 1 also reacts with alcohols, dienes and oxygen but is less susceptible to polymerizatiopn than 2. Enhanced chemical reactivity of dimetyl{; ; ; 3.1.1}; ; ; -propellane 1, with respect to its unsubstituted analogue 2, is in accord with an increase in nucleophilicity of its central bond due to electron donation of the methyl groups.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA