Cyclobutanone-based tandem free radical rearrangements: Formation of bicyclic and tricyclic ketones

Paul Dowd; Wei Zhang; Khalid Mahmood

doi:10.1016/0040-4020(94)00961-S

Cyclobutanone-based tandem free radical rearrangements: Formation of bicyclic and tricyclic ketones

Paul Dowd
, Wei Zhang
, Khalid Mahmood

Chemistry

University of Pittsburgh

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

Abstract

Free radical reaction of endo-bromopropylbicyclo[4.2.0]oct-2-en-7-one 1 leads to deep-seated rearrangement and formation of the bridged tricyclic ketone 2. An authentic sample of 2 was prepared. Reaction of endobromoethylbicyclo[4.2.0]oct-2-en-7-one 18 generates an analogous bridged tricyclic ketone 20 together with cis-bicyclo[4.4.0]decenone 22. Experiments using Bu₃SnD were carried out to explore the mechanism of the transformation leading to 22.

Original language	English
Pages (from-to)	39-50
Number of pages	12
Journal	Tetrahedron
Volume	51
Issue number	1
DOIs	https://doi.org/10.1016/0040-4020(94)00961-S
State	Published - Jan 2 1995

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Cyclobutanone-based tandem free radical rearrangements: Formation of bicyclic and tricyclic ketones",

abstract = "Free radical reaction of endo-bromopropylbicyclo[4.2.0]oct-2-en-7-one 1 leads to deep-seated rearrangement and formation of the bridged tricyclic ketone 2. An authentic sample of 2 was prepared. Reaction of endobromoethylbicyclo[4.2.0]oct-2-en-7-one 18 generates an analogous bridged tricyclic ketone 20 together with cis-bicyclo[4.4.0]decenone 22. Experiments using Bu3SnD were carried out to explore the mechanism of the transformation leading to 22.",

author = "Paul Dowd and Wei Zhang and Khalid Mahmood",

year = "1995",

month = jan,

day = "2",

doi = "10.1016/0040-4020(94)00961-S",

language = "English",

volume = "51",

pages = "39--50",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "1",

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T1 - Cyclobutanone-based tandem free radical rearrangements

T2 - Formation of bicyclic and tricyclic ketones

AU - Dowd, Paul

AU - Zhang, Wei

AU - Mahmood, Khalid

PY - 1995/1/2

Y1 - 1995/1/2

N2 - Free radical reaction of endo-bromopropylbicyclo[4.2.0]oct-2-en-7-one 1 leads to deep-seated rearrangement and formation of the bridged tricyclic ketone 2. An authentic sample of 2 was prepared. Reaction of endobromoethylbicyclo[4.2.0]oct-2-en-7-one 18 generates an analogous bridged tricyclic ketone 20 together with cis-bicyclo[4.4.0]decenone 22. Experiments using Bu3SnD were carried out to explore the mechanism of the transformation leading to 22.

AB - Free radical reaction of endo-bromopropylbicyclo[4.2.0]oct-2-en-7-one 1 leads to deep-seated rearrangement and formation of the bridged tricyclic ketone 2. An authentic sample of 2 was prepared. Reaction of endobromoethylbicyclo[4.2.0]oct-2-en-7-one 18 generates an analogous bridged tricyclic ketone 20 together with cis-bicyclo[4.4.0]decenone 22. Experiments using Bu3SnD were carried out to explore the mechanism of the transformation leading to 22.

UR - https://www.scopus.com/pages/publications/0028861727

UR - https://www.scopus.com/pages/publications/0028861727#tab=citedBy

U2 - 10.1016/0040-4020(94)00961-S

DO - 10.1016/0040-4020(94)00961-S

M3 - Article

AN - SCOPUS:0028861727

SN - 0040-4020

VL - 51

SP - 39

EP - 50

JO - Tetrahedron

JF - Tetrahedron

IS - 1

ER -

Cyclobutanone-based tandem free radical rearrangements: Formation of bicyclic and tricyclic ketones

Abstract

ASJC Scopus Subject Areas

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