Bicyclo[3.2.1]octane Synthons from Cyclopropenes: Functionalization of Cycloadducts by Nucleophilic Additions
- 30 December 2003
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (2), 406-416
- https://doi.org/10.1021/jo035240m
Abstract
It has been known for several decades that a highly functionalized family of tetrahalobicyclo[3.2.1]octadienes are readily available through the cycloaddition of furan or cyclopentadiene with either tetrachloro- or tetrabromocyclopropene. However, the application of these highly functionalized building blocks in synthesis has remained relatively unexplored in relation to their better-known counterparts derived through oxyallyl cation additions. As a first step toward utilizing these highly versatile intermediates in synthesis, a study of the addition of various nucleophiles to the halogenated nucleus has been conducted. It has been found that these halogenated systems are amenable to a wide range of functionalizations in high yields and with good selectivities.Keywords
This publication has 40 references indexed in Scilit:
- Asymmetric Organocatalysis of 4 + 3 Cycloaddition ReactionsJournal of the American Chemical Society, 2003
- Synthesis of Functionalized Pyrans by Domino Metathesis Reaction of Oxabicyclo Derivatives: Dramatic Effect of Remote Substituents on Reactivity and SelectivityAngewandte Chemie, 2002
- New Applications of Polyfunctional Organometallic Compounds in Organic SynthesisAngewandte Chemie, 2000
- Synthesis and fluorine NMR chemical shifts for a series of exo-3,3-difluorotricyclo[3.2.1.02,4]octyl derivatives: The Diels–Alder alternative to difluorocarbene additionsJournal of Fluorine Chemistry, 2000
- Mechanism of conjugate additions of dialkylcuprates to bromonaphthoquinonesThe Journal of Organic Chemistry, 1991
- Reactions of dialkylmagnesium-salt mixtures with ketones: increasing the ratio of addition to reductionThe Journal of Organic Chemistry, 1990
- Synthesis of useful building blocks for monofluorinated compounds derived from trifluoroetheneJournal of Fluorine Chemistry, 1985
- Relative Rates of Grignard Addition and Reduction Reactions1-3Journal of the American Chemical Society, 1961
- THE REDUCING ACTION OF THE GRIGNARD REAGENT. III. HYDROCARBONS FORMED DURING REDUCTIONJournal of the American Chemical Society, 1932
- THE REDUCING ACTION AND CONSTITUTION OF THE GRIGNARD REAGENTJournal of the American Chemical Society, 1931