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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.