Synthese von [ n .1.1]Propellanen ( n  = 2, 3, 4) | Zendy

Fuchs Josef | Zendy; Szeimies Günter | Zendy

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Synthese von [ n .1.1]Propellanen ( n = 2, 3, 4)

Author(s) -

Fuchs Josef,

Szeimies Günter

Publication year - 1992

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19921251126

Subject(s) - oxetane , chemistry , paraformaldehyde , propellane , ethylene , ethylene oxide , medicinal chemistry , alcohol , stereochemistry , bicyclic molecule , polymer chemistry , organic chemistry , catalysis , polymer , copolymer

A facile access to the parent [ n .1.1]propellanes 2, 3 and 4 is presented. Lithiation of methallyl alcohol with the BuLi/TMEDA complex and reaction of the organometallic intermediate 8 with paraformaldehyde, ethylene oxide, or oxetane affords the diols 9 which are converted via the dichlorides 10 into the tetrahalides 11 . The cyclization of 11 to the corresponding propellanes is effected with 2 equiv. of MeLi or BuLi via the bromobicyclo[1.1.0]butanes 12 . As expected, 2 cannot be isolated; its formation is deduced from the structure of the consecutive products.

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