5-Methylene-2(5H)-furanone as a Dienophile in Diels-Alder Cycloadditions: Site Selectivity and Regioselectivity

Daniel Alonso; Juan Orti; Vicenc Branchadell; Antonio Oliva; Rosa M. Ortuno; Juan Bertran; Josep Font

doi:10.1021/jo00297a021

5-Methylene-2(5H)-furanone as a Dienophile in Diels-Alder Cycloadditions: Site Selectivity and Regioselectivity

Daniel Alonso, Juan Orti, Vicenc Branchadell, Antonio Oliva, Rosa M. Ortuno, Juan Bertran, Josep Font

Department of Chemistry

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

27 Citations (Scopus)

Abstract

Site selectivity and regioselectivity in Diels-Alder reactions of 5-methylene-2(5H)-furanone (1) with several acyclic dienes have been investigated. We have found that I consistently reacts specifically at the exocyclic double bond, giving spiro adducts in good yields. Excellent regioselectivity has also been found in either catalyzed or uncatalyzed reactions with unsymmetrically substituted dienes. A kinetic study of the reaction with isoprene has revealed that the observed regioselectivity is a direct consequence of kinetic control over the process. Theoretical calculations have been carried out in order to interpret these experimental results. © 1990, American Chemical Society. All rights reserved.

Original language	English
Pages (from-to)	3060-3063
Journal	Journal of Organic Chemistry
Volume	55
Issue number	10
DOIs	https://doi.org/10.1021/jo00297a021
Publication status	Published - 1 Jan 1990

Access to Document

10.1021/jo00297a021

Cite this

@article{bc117a92b86b4dcda8216b6f6dfc48a2,

title = "5-Methylene-2(5H)-furanone as a Dienophile in Diels-Alder Cycloadditions: Site Selectivity and Regioselectivity",

abstract = "Site selectivity and regioselectivity in Diels-Alder reactions of 5-methylene-2(5H)-furanone (1) with several acyclic dienes have been investigated. We have found that I consistently reacts specifically at the exocyclic double bond, giving spiro adducts in good yields. Excellent regioselectivity has also been found in either catalyzed or uncatalyzed reactions with unsymmetrically substituted dienes. A kinetic study of the reaction with isoprene has revealed that the observed regioselectivity is a direct consequence of kinetic control over the process. Theoretical calculations have been carried out in order to interpret these experimental results. {\textcopyright} 1990, American Chemical Society. All rights reserved.",

author = "Daniel Alonso and Juan Orti and Vicenc Branchadell and Antonio Oliva and Ortuno, {Rosa M.} and Juan Bertran and Josep Font",

year = "1990",

month = jan,

day = "1",

doi = "10.1021/jo00297a021",

language = "English",

volume = "55",

pages = "3060--3063",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "10",

}

TY - JOUR

T1 - 5-Methylene-2(5H)-furanone as a Dienophile in Diels-Alder Cycloadditions: Site Selectivity and Regioselectivity

AU - Alonso, Daniel

AU - Orti, Juan

AU - Branchadell, Vicenc

AU - Oliva, Antonio

AU - Ortuno, Rosa M.

AU - Bertran, Juan

AU - Font, Josep

PY - 1990/1/1

Y1 - 1990/1/1

N2 - Site selectivity and regioselectivity in Diels-Alder reactions of 5-methylene-2(5H)-furanone (1) with several acyclic dienes have been investigated. We have found that I consistently reacts specifically at the exocyclic double bond, giving spiro adducts in good yields. Excellent regioselectivity has also been found in either catalyzed or uncatalyzed reactions with unsymmetrically substituted dienes. A kinetic study of the reaction with isoprene has revealed that the observed regioselectivity is a direct consequence of kinetic control over the process. Theoretical calculations have been carried out in order to interpret these experimental results. © 1990, American Chemical Society. All rights reserved.

AB - Site selectivity and regioselectivity in Diels-Alder reactions of 5-methylene-2(5H)-furanone (1) with several acyclic dienes have been investigated. We have found that I consistently reacts specifically at the exocyclic double bond, giving spiro adducts in good yields. Excellent regioselectivity has also been found in either catalyzed or uncatalyzed reactions with unsymmetrically substituted dienes. A kinetic study of the reaction with isoprene has revealed that the observed regioselectivity is a direct consequence of kinetic control over the process. Theoretical calculations have been carried out in order to interpret these experimental results. © 1990, American Chemical Society. All rights reserved.

U2 - 10.1021/jo00297a021

DO - 10.1021/jo00297a021

M3 - Article

SN - 0022-3263

VL - 55

SP - 3060

EP - 3063

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 10

ER -

5-Methylene-2(5H)-furanone as a Dienophile in Diels-Alder Cycloadditions: Site Selectivity and Regioselectivity

Abstract

Access to Document

Fingerprint

Cite this