Formation of Organomagnesium Compounds via EtMgBr-Mediated Radical Cyclization of Allyl β-Iodoacetals
- 8 February 2000
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (5) , 651-653
- https://doi.org/10.1021/ol991403a
Abstract
Treatment of allyl β-iodoacetals with ethylmagnesium bromide in THF provided tetrahydrofuran derivatives in good yields. On the other hand, the reaction in DME provided tetrahydrofuranylmethylmagnesium compounds in good yields.Keywords
This publication has 21 references indexed in Scilit:
- Stereoselective Preparation of Functionalized Alkenylmagnesium Reagents via an Iodine−Magnesium Exchange ReactionThe Journal of Organic Chemistry, 1999
- Catalytic Cycloisomerization of Unsaturated OrganoiodidesThe Journal of Organic Chemistry, 1998
- Lithium−Iodine Exchange Mediated Atom Transfer Cyclization: Catalytic Cycloisomerization of 6-Iodo-1-hexenesThe Journal of Organic Chemistry, 1998
- Stereoselective intermolecular radical additions to amide-substituted alkenesJournal of the American Chemical Society, 1991
- Radical Cyclizations and Sequential Radical ReactionsPublished by Elsevier ,1991
- Asymmetric radical addition, cyclization, and annulation reactions with Oppolzer's camphor sultamJournal of the American Chemical Society, 1990
- Mechanism of the Grignard reactionJournal of Physical Organic Chemistry, 1989
- A critical evaluation of studies employing alkenyl halide "mechanistic probes" as indicators of single-electron-transfer processesAccounts of Chemical Research, 1988
- Radical cyclization-trapping in the synthesis of natural products. A simple, stereocontrolled route to prostaglandin F2.alpha.Journal of the American Chemical Society, 1986
- Mechanisms of Grignard reagent addition to ketonesAccounts of Chemical Research, 1974