The debromination route to norbornadienomaleimides and 7-oxanorbornadienomaleimides: Study of cycloaddition specificities with cyclic dienes.

Ronald N. Warrener, Gordon M. Elsey, Ljiljana Maksimovic, Martin R. Johnston, Colin H.L. Kennard

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

The debromination route (Zn/Ag in THF) which successfully produces 7-oxanorbomadienes fails in the norbornadiene series owing to different stereochemical positioning of the bromine substituents in the bicyclic precursors. A new oxygen, oxygen repulsive interaction is proposed to play a dominant but not exclusive role in determining stereochemical outcomes in the cycloaddition of 7-oxanorbomadienomaleimides with cyclopentadiene, furan and 2,5-dimethylfuran. The major product observed experimentally is in complete accord with that predicted by semi-empirical molecular orbital calculations (AM1).

Original languageEnglish
Pages (from-to)7753-7756
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number42
DOIs
Publication statusPublished - 16 Oct 1995
Externally publishedYes

Fingerprint Dive into the research topics of 'The debromination route to norbornadienomaleimides and 7-oxanorbornadienomaleimides: Study of cycloaddition specificities with cyclic dienes.'. Together they form a unique fingerprint.

Cite this