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

doi:10.1016/0040-4039(95)01617-Q

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 journal › Article › peer-review

17 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 language	English
Pages (from-to)	7753-7756
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	42
DOIs	https://doi.org/10.1016/0040-4039(95)01617-Q
Publication status	Published - 16 Oct 1995
Externally published	Yes

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

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).",

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T1 - The debromination route to norbornadienomaleimides and 7-oxanorbornadienomaleimides

T2 - Study of cycloaddition specificities with cyclic dienes.

AU - Warrener, Ronald N.

AU - Elsey, Gordon M.

AU - Maksimovic, Ljiljana

AU - Johnston, Martin R.

AU - Kennard, Colin H.L.

PY - 1995/10/16

Y1 - 1995/10/16

N2 - 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).

AB - 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).

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 42

ER -

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

Abstract

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