Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 55, No. 8, 2001, pp.1467-1474
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9232
Remarkably Easy Oxidation of Alkylzinc Reagents in Their Reactions with Electrophiles to Produce Alkoxylated Instead of the Expected Alkylated Products

Alan R. Katritzky* and Zhushou Luo

*Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, U.S.A.


Alkylzinc reagents, in contrast to arylzinc reagents, react with two series of α-benzotriazolylalkylamines to give oxidized products formed by the incorporation of an atom of oxygen into the carbon-zinc bond even when the reactions are carried out under argon. Thus, benzotriazole derivatives of 4,5-disubstituted imidazolidinone (2) and N-Boc-2-benzotriazolylpyrrolidine (7) gave oxidized products (4a-b) and (8a-c), respectively. The abnormal reaction course was traced to molecular oxygen dissolved in the THF. The expected, unoxidized products (9a-d) were obtained under rigorous argon purge of the THF solvent and solutions.