Elimination versus ring opening: A convergent route to alkylidene- cyclobutanes

Julien Brioche; Michal Michalak; Béatrice Quiclet-Sire; Samir Z. Zard

doi:10.1021/ol202798r

Elimination versus ring opening: A convergent route to alkylidene- cyclobutanes

Julien Brioche
, Michal Michalak
, Béatrice Quiclet-Sire
, Samir Z. Zard

Laboratoire de Synthèse Organique

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

Abstract

Functionalized alkylidene-cyclobutanes have been prepared from 2-fluoropyridinyl-6-oxy precursors derived from vinyl cyclobutanols by a radical addition-elimination process. A wide range of functional groups is tolerated, and the alkylidene-cyclobutanes can be further elaborated into cyclopentanones. The limitation of this approach resides in the competition with opening of the cyclobutane ring.

Original language	English
Pages (from-to)	6296-6299
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	23
DOIs	https://doi.org/10.1021/ol202798r
Publication status	Published - 2 Dec 2011
Externally published	Yes

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@article{a522baf06484486dadeb4912cba95d9e,

title = "Elimination versus ring opening: A convergent route to alkylidene- cyclobutanes",

abstract = "Functionalized alkylidene-cyclobutanes have been prepared from 2-fluoropyridinyl-6-oxy precursors derived from vinyl cyclobutanols by a radical addition-elimination process. A wide range of functional groups is tolerated, and the alkylidene-cyclobutanes can be further elaborated into cyclopentanones. The limitation of this approach resides in the competition with opening of the cyclobutane ring.",

author = "Julien Brioche and Michal Michalak and B{\'e}atrice Quiclet-Sire and Zard, \{Samir Z.\}",

year = "2011",

month = dec,

day = "2",

doi = "10.1021/ol202798r",

language = "English",

volume = "13",

pages = "6296--6299",

journal = "Organic Letters",

issn = "1523-7060",

number = "23",

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T1 - Elimination versus ring opening

T2 - A convergent route to alkylidene- cyclobutanes

AU - Brioche, Julien

AU - Michalak, Michal

AU - Quiclet-Sire, Béatrice

AU - Zard, Samir Z.

PY - 2011/12/2

Y1 - 2011/12/2

N2 - Functionalized alkylidene-cyclobutanes have been prepared from 2-fluoropyridinyl-6-oxy precursors derived from vinyl cyclobutanols by a radical addition-elimination process. A wide range of functional groups is tolerated, and the alkylidene-cyclobutanes can be further elaborated into cyclopentanones. The limitation of this approach resides in the competition with opening of the cyclobutane ring.

AB - Functionalized alkylidene-cyclobutanes have been prepared from 2-fluoropyridinyl-6-oxy precursors derived from vinyl cyclobutanols by a radical addition-elimination process. A wide range of functional groups is tolerated, and the alkylidene-cyclobutanes can be further elaborated into cyclopentanones. The limitation of this approach resides in the competition with opening of the cyclobutane ring.

U2 - 10.1021/ol202798r

DO - 10.1021/ol202798r

M3 - Article

AN - SCOPUS:82355168545

SN - 1523-7060

VL - 13

SP - 6296

EP - 6299

JO - Organic Letters

JF - Organic Letters

IS - 23

ER -

Elimination versus ring opening: A convergent route to alkylidene- cyclobutanes

Abstract

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