Reversible cyclopropane ring-cleavage reactions within etheno-bridged [4.3.1]propelladiene frameworks leading to aza- and oxa-[5.6.5.6] fenestratetraenes

Nora Heinrich; Anthony C. Willis; Ian A. Cade; Junming Ho; Michelle L. Coote; Martin G. Banwell

doi:10.1002/chem.201202903

Reversible cyclopropane ring-cleavage reactions within etheno-bridged [4.3.1]propelladiene frameworks leading to aza- and oxa-[5.6.5.6] fenestratetraenes

Nora Heinrich, Anthony C. Willis, Ian A. Cade, Junming Ho, Michelle L. Coote, Martin G. Banwell^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

Opening and closing a chemical window: Oxidation of the etheno-bridged [4.3.1]propelladienol 1 with pyridinium chlorochromate (PCC) affords oxa[5.6.5.6]fenestratetraene 2. The reduction of 2 with diisobutylaluminum hydride (DIBAl-H) leads to the regeneration of its precursor (1; see scheme). These transformations most likely involve a [3,5]-sigmatropic rearrangement process.

Original language	English
Pages (from-to)	13585-13588
Number of pages	4
Journal	Chemistry - A European Journal
Volume	18
Issue number	43
DOIs	https://doi.org/10.1002/chem.201202903
Publication status	Published - 22 Oct 2012

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title = "Reversible cyclopropane ring-cleavage reactions within etheno-bridged [4.3.1]propelladiene frameworks leading to aza- and oxa-[5.6.5.6] fenestratetraenes",

abstract = "Opening and closing a chemical window: Oxidation of the etheno-bridged [4.3.1]propelladienol 1 with pyridinium chlorochromate (PCC) affords oxa[5.6.5.6]fenestratetraene 2. The reduction of 2 with diisobutylaluminum hydride (DIBAl-H) leads to the regeneration of its precursor (1; see scheme). These transformations most likely involve a [3,5]-sigmatropic rearrangement process.",

keywords = "cleavage reactions, fenestratetraenes, norcaradienes, salvileucalin B, sigmatropic rearrangement",

author = "Nora Heinrich and Willis, {Anthony C.} and Cade, {Ian A.} and Junming Ho and Coote, {Michelle L.} and Banwell, {Martin G.}",

year = "2012",

month = oct,

day = "22",

doi = "10.1002/chem.201202903",

language = "English",

volume = "18",

pages = "13585--13588",

journal = "Chemistry - A European Journal",

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T1 - Reversible cyclopropane ring-cleavage reactions within etheno-bridged [4.3.1]propelladiene frameworks leading to aza- and oxa-[5.6.5.6] fenestratetraenes

AU - Heinrich, Nora

AU - Willis, Anthony C.

AU - Cade, Ian A.

AU - Ho, Junming

AU - Coote, Michelle L.

AU - Banwell, Martin G.

PY - 2012/10/22

Y1 - 2012/10/22

N2 - Opening and closing a chemical window: Oxidation of the etheno-bridged [4.3.1]propelladienol 1 with pyridinium chlorochromate (PCC) affords oxa[5.6.5.6]fenestratetraene 2. The reduction of 2 with diisobutylaluminum hydride (DIBAl-H) leads to the regeneration of its precursor (1; see scheme). These transformations most likely involve a [3,5]-sigmatropic rearrangement process.

AB - Opening and closing a chemical window: Oxidation of the etheno-bridged [4.3.1]propelladienol 1 with pyridinium chlorochromate (PCC) affords oxa[5.6.5.6]fenestratetraene 2. The reduction of 2 with diisobutylaluminum hydride (DIBAl-H) leads to the regeneration of its precursor (1; see scheme). These transformations most likely involve a [3,5]-sigmatropic rearrangement process.

KW - cleavage reactions

KW - fenestratetraenes

KW - norcaradienes

KW - salvileucalin B

KW - sigmatropic rearrangement

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DO - 10.1002/chem.201202903

M3 - Article

SN - 0947-6539

VL - 18

SP - 13585

EP - 13588

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 43

ER -

Reversible cyclopropane ring-cleavage reactions within etheno-bridged [4.3.1]propelladiene frameworks leading to aza- and oxa-[5.6.5.6] fenestratetraenes

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