ISSN:
0009-2940
Keywords:
[2.2]Paracyclophanes
;
1,2-Dibromoarenes
;
anti-[2.2]Paracyclophanes
;
Aryne generation
;
Diels-Alder reactions
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The reaction of 2 with nBuLi 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.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931261130
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