Premium
4,5,12,13‐Tetrabromo[2.2]paracyclophane – A New Bis(aryne) Equivalent
Author(s) -
König Burkhard,
Knieriem Burkhard,
Rauch Karsten,
Meijere Armin De
Publication year - 1993
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.19931261130
Subject(s) - aryne , chemistry , furan , cyclopentadiene , isobenzofuran , deoxygenation , medicinal chemistry , adduct , reagent , aromaticity , photochemistry , organic chemistry , molecule , catalysis
The reaction of 2 with n BuLi at –78°C generates aryne intermediates within the aromatic rings of [2.2]paracyclophane which are trapped in Diels‐Alder reactions with dienes like furan, 1,9‐diphenylisobenzofuran, or cyclopentadiene. Reductive deoxygenation with low‐valent titanium reagents or TMSI converts the adducts of furan and isobenzofuran into anti ‐[2.2]paracyclophanes 4 and 5 , respectively. The reaction of two aryne intermediates with [2.2](2,5)furanophane ( 7 ) yields 8 with three [2.2]paracyclophane units arranged in a stair‐like fashion; yet, in this compound the highly shielded oxygen atoms cannot be removed anymore by reduction.