Intramolecular [2+2]-cycloaddition of propargylic 2,3-allenoates for the efficient synthesis of 3-oxabicyclo[4.2.0]octa-1(8),5-dien-4-ones: a dramatic substituent effect

Xuefeng Jiang; Shengming Ma

doi:10.1016/j.tet.2007.05.040

Intramolecular [2+2]-cycloaddition of propargylic 2,3-allenoates for the efficient synthesis of 3-oxabicyclo[4.2.0]octa-1(8),5-dien-4-ones: a dramatic substituent effect

Xuefeng Jiang
, Shengming Ma^*

^*Corresponding author for this work

CAS - Shanghai Institute of Organic Chemistry

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

37 Scopus citations

Abstract

[2+2]-Cycloaddition reactions of propargylic 2,3-allenoates under conventional heating conditions afforded 3-oxabicyclo[4.2.0]octa-1(8),5-dien-4-ones, which contain both the biologically important 5,6-dihydropyran-2-one and cyclobutene units.

Original language	English
Pages (from-to)	7589-7595
Number of pages	7
Journal	Tetrahedron
Volume	63
Issue number	32
DOIs	https://doi.org/10.1016/j.tet.2007.05.040
State	Published - 6 Aug 2007
Externally published	Yes

Keywords

5,6-Dihydropyran-2-one
Cyclobutene
Heat of formation
Propargylic 2,3-allenoate
[2+2]-Cycloaddition

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10.1016/j.tet.2007.05.040

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@article{938bba049189403b9bd319200a5d1dcb,

title = "Intramolecular [2+2]-cycloaddition of propargylic 2,3-allenoates for the efficient synthesis of 3-oxabicyclo[4.2.0]octa-1(8),5-dien-4-ones: a dramatic substituent effect",

abstract = "[2+2]-Cycloaddition reactions of propargylic 2,3-allenoates under conventional heating conditions afforded 3-oxabicyclo[4.2.0]octa-1(8),5-dien-4-ones, which contain both the biologically important 5,6-dihydropyran-2-one and cyclobutene units.",

keywords = "5,6-Dihydropyran-2-one, Cyclobutene, Heat of formation, Propargylic 2,3-allenoate, [2+2]-Cycloaddition",

author = "Xuefeng Jiang and Shengming Ma",

year = "2007",

month = aug,

day = "6",

doi = "10.1016/j.tet.2007.05.040",

language = "英语",

volume = "63",

pages = "7589--7595",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "32",

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TY - JOUR

T1 - Intramolecular [2+2]-cycloaddition of propargylic 2,3-allenoates for the efficient synthesis of 3-oxabicyclo[4.2.0]octa-1(8),5-dien-4-ones

T2 - a dramatic substituent effect

AU - Jiang, Xuefeng

AU - Ma, Shengming

PY - 2007/8/6

Y1 - 2007/8/6

N2 - [2+2]-Cycloaddition reactions of propargylic 2,3-allenoates under conventional heating conditions afforded 3-oxabicyclo[4.2.0]octa-1(8),5-dien-4-ones, which contain both the biologically important 5,6-dihydropyran-2-one and cyclobutene units.

AB - [2+2]-Cycloaddition reactions of propargylic 2,3-allenoates under conventional heating conditions afforded 3-oxabicyclo[4.2.0]octa-1(8),5-dien-4-ones, which contain both the biologically important 5,6-dihydropyran-2-one and cyclobutene units.

KW - 5,6-Dihydropyran-2-one

KW - Cyclobutene

KW - Heat of formation

KW - Propargylic 2,3-allenoate

KW - [2+2]-Cycloaddition

UR - https://www.scopus.com/pages/publications/34250755358

U2 - 10.1016/j.tet.2007.05.040

DO - 10.1016/j.tet.2007.05.040

M3 - 文章

AN - SCOPUS:34250755358

SN - 0040-4020

VL - 63

SP - 7589

EP - 7595

JO - Tetrahedron

JF - Tetrahedron

IS - 32

ER -

Intramolecular [2+2]-cycloaddition of propargylic 2,3-allenoates for the efficient synthesis of 3-oxabicyclo[4.2.0]octa-1(8),5-dien-4-ones: a dramatic substituent effect

Abstract

Keywords

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