Journal article
Self-Addition of a Sterically Hindered Alkynylselenolate.



Publication Details
Authors:
Pietschnig, R.; Schäfer, S.; Merz, K.
Publisher:
American Chemical SocietyDO - 10.1021/ol034476+
Publication year:
2003
Journal:
Organic Letters
Pages range:
1867-1869
Volume number:
5
Start page:
1867
End page:
1869
ISSN:
1523-7060

Abstract
The unprecedented formation of a complex macrocyclic selenium-carbon ring system, which is initiated by the action of coordinating reagents upon a sterically hindered alkynylselenolate, was obsd. Reaction of 2-ethynyl-1,3,5-triisopropylbenzene with BuLi followed by elemental Se gave lithium (2,4,6-triisopropylphenyl)ethynylselenolate (2), which gave selenium macrocycle 3 (shown as I) on action of TMEDA. The crystal structure of the product 3 was obtained and shows a rigid tricyclic arrangement consisting only of selenium and sp2-hybridized carbon atoms. This reactivity stands in contrast to the corresponding unsubstituted alkynylselenolates and is an example where a bulky substituent destabilizes an adjacent unsatd. π-system. [on SciFinder(R)]


Keywords
crystal structure octaselena cyclohexadecatetraene macrocycle triisopropylphenyl deriv, cyclocondensation lithium ethynylselenolate decaselenium macrocycle prepn, selenium macrocycle octaselena cyclohexadecatetraene prepn cyclocondensation ethynylselenolate


Authors/Editors

Last updated on 2019-25-07 at 16:02