Photochemical Hexadehydro-Diels-Alder Reaction

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

We demonstrate that the hexadehydro-Diels-Alder (HDDA) cycloisomerization reaction to produce reactive benzyne derivatives can be initiated photochemically. As with the thermal variant of the HDDA process, the reactive intermediates are formed in the absence of reagents or the resulting byproducts required for the generation of benzynes by traditional methods. This photo-HDDA (or hν-HDDA) reaction occurs at much lower temperatures (including even at -70 °C) than the thermal HDDA, but the benzynes produced behave in the same fashion with respect to their trapping reactions, suggesting they are of the same electronic state.

Original languageEnglish (US)
Pages (from-to)8400-8403
Number of pages4
JournalJournal of the American Chemical Society
Volume139
Issue number25
DOIs
StatePublished - Jun 28 2017

Fingerprint

Alnus
Cycloaddition Reaction
Electronic states
Hot Temperature
Byproducts
Derivatives
Temperature
benzyne

Cite this

Photochemical Hexadehydro-Diels-Alder Reaction. / Xu, Feng; Xiao, Xiao; Hoye, Thomas R.

In: Journal of the American Chemical Society, Vol. 139, No. 25, 28.06.2017, p. 8400-8403.

Research output: Contribution to journalArticle

@article{2321c5500cbd49b1b130e26ee055c09f,
title = "Photochemical Hexadehydro-Diels-Alder Reaction",
abstract = "We demonstrate that the hexadehydro-Diels-Alder (HDDA) cycloisomerization reaction to produce reactive benzyne derivatives can be initiated photochemically. As with the thermal variant of the HDDA process, the reactive intermediates are formed in the absence of reagents or the resulting byproducts required for the generation of benzynes by traditional methods. This photo-HDDA (or hν-HDDA) reaction occurs at much lower temperatures (including even at -70 °C) than the thermal HDDA, but the benzynes produced behave in the same fashion with respect to their trapping reactions, suggesting they are of the same electronic state.",
author = "Feng Xu and Xiao Xiao and Hoye, {Thomas R}",
year = "2017",
month = "6",
day = "28",
doi = "10.1021/jacs.7b03832",
language = "English (US)",
volume = "139",
pages = "8400--8403",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "25",

}

TY - JOUR

T1 - Photochemical Hexadehydro-Diels-Alder Reaction

AU - Xu, Feng

AU - Xiao, Xiao

AU - Hoye, Thomas R

PY - 2017/6/28

Y1 - 2017/6/28

N2 - We demonstrate that the hexadehydro-Diels-Alder (HDDA) cycloisomerization reaction to produce reactive benzyne derivatives can be initiated photochemically. As with the thermal variant of the HDDA process, the reactive intermediates are formed in the absence of reagents or the resulting byproducts required for the generation of benzynes by traditional methods. This photo-HDDA (or hν-HDDA) reaction occurs at much lower temperatures (including even at -70 °C) than the thermal HDDA, but the benzynes produced behave in the same fashion with respect to their trapping reactions, suggesting they are of the same electronic state.

AB - We demonstrate that the hexadehydro-Diels-Alder (HDDA) cycloisomerization reaction to produce reactive benzyne derivatives can be initiated photochemically. As with the thermal variant of the HDDA process, the reactive intermediates are formed in the absence of reagents or the resulting byproducts required for the generation of benzynes by traditional methods. This photo-HDDA (or hν-HDDA) reaction occurs at much lower temperatures (including even at -70 °C) than the thermal HDDA, but the benzynes produced behave in the same fashion with respect to their trapping reactions, suggesting they are of the same electronic state.

UR - http://www.scopus.com/inward/record.url?scp=85021661071&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85021661071&partnerID=8YFLogxK

U2 - 10.1021/jacs.7b03832

DO - 10.1021/jacs.7b03832

M3 - Article

C2 - 28548500

AN - SCOPUS:85021661071

VL - 139

SP - 8400

EP - 8403

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 25

ER -