The preparation and thermolysis reactions of allyl 3,4,5,6,7,8- hexafluoroquinolin-2-yl ether, allyl 2,3,5,6,7,8- hexafluoroquinolin-4-yl ether and allyl 3,4,5,6,7,8- hexafluoroisoquinolin-1-yl ether

Gerald M. Brooke, Ian Eggleston, Francis I. Hale

Research output: Contribution to journalArticle

Abstract

Sodium allyl oxide reacted with 2,3,4,5,6,7,8-heptafluoroquinoline to give allyl 3,4,5,6,7,8-hexafluoroquinolin-2-yl ether (7) and allyl 2,3,5,6,7,8-hexafluoroquinolin-4-yl ether (8) in the ratio 3.4:1 respectively, and with 1,3,4,5,6,7,8-heptafluoroisoquinoline to give allyl 3,4,5,6,7,8-hexafluoroisoquinolin- 1- yl ether (9). Thermolyses of (7) and (9) in tetralin at 212°C gave the Claisen rearrangement products (10) and (12) in which nitrogen is the migration terminus, in slow reactions over 48 h, whereas the isomerisation of (8) to (11) in which carbon is the migration terminus, was complete within 2.5 h at 147.5°C. Compound (11) is very susceptible to hydrolysis, giving with undried toluene, the dione (13) containing half a molecule of solvent toluene.
Original languageEnglish
Pages (from-to)421
Number of pages434
JournalJournal of Fluorine Chemistry
Volume38
Issue number3
DOIs
Publication statusPublished - 1988

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Thermolysis
ether
Ether
ethers
Toluene
toluene
preparation
Dione
Isomerization
Oxides
isomerization
hydrolysis
Hydrolysis
Nitrogen
Carbon
Sodium
sodium
oxide
nitrogen
Molecules

Cite this

@article{e2c2dbdc62914cd9a01f852c7ce5ecee,
title = "The preparation and thermolysis reactions of allyl 3,4,5,6,7,8- hexafluoroquinolin-2-yl ether, allyl 2,3,5,6,7,8- hexafluoroquinolin-4-yl ether and allyl 3,4,5,6,7,8- hexafluoroisoquinolin-1-yl ether",
abstract = "Sodium allyl oxide reacted with 2,3,4,5,6,7,8-heptafluoroquinoline to give allyl 3,4,5,6,7,8-hexafluoroquinolin-2-yl ether (7) and allyl 2,3,5,6,7,8-hexafluoroquinolin-4-yl ether (8) in the ratio 3.4:1 respectively, and with 1,3,4,5,6,7,8-heptafluoroisoquinoline to give allyl 3,4,5,6,7,8-hexafluoroisoquinolin- 1- yl ether (9). Thermolyses of (7) and (9) in tetralin at 212°C gave the Claisen rearrangement products (10) and (12) in which nitrogen is the migration terminus, in slow reactions over 48 h, whereas the isomerisation of (8) to (11) in which carbon is the migration terminus, was complete within 2.5 h at 147.5°C. Compound (11) is very susceptible to hydrolysis, giving with undried toluene, the dione (13) containing half a molecule of solvent toluene.",
author = "Brooke, {Gerald M.} and Ian Eggleston and Hale, {Francis I.}",
year = "1988",
doi = "10.1016/S0022-1139(00)81077-5",
language = "English",
volume = "38",
pages = "421",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier",
number = "3",

}

TY - JOUR

T1 - The preparation and thermolysis reactions of allyl 3,4,5,6,7,8- hexafluoroquinolin-2-yl ether, allyl 2,3,5,6,7,8- hexafluoroquinolin-4-yl ether and allyl 3,4,5,6,7,8- hexafluoroisoquinolin-1-yl ether

AU - Brooke, Gerald M.

AU - Eggleston, Ian

AU - Hale, Francis I.

PY - 1988

Y1 - 1988

N2 - Sodium allyl oxide reacted with 2,3,4,5,6,7,8-heptafluoroquinoline to give allyl 3,4,5,6,7,8-hexafluoroquinolin-2-yl ether (7) and allyl 2,3,5,6,7,8-hexafluoroquinolin-4-yl ether (8) in the ratio 3.4:1 respectively, and with 1,3,4,5,6,7,8-heptafluoroisoquinoline to give allyl 3,4,5,6,7,8-hexafluoroisoquinolin- 1- yl ether (9). Thermolyses of (7) and (9) in tetralin at 212°C gave the Claisen rearrangement products (10) and (12) in which nitrogen is the migration terminus, in slow reactions over 48 h, whereas the isomerisation of (8) to (11) in which carbon is the migration terminus, was complete within 2.5 h at 147.5°C. Compound (11) is very susceptible to hydrolysis, giving with undried toluene, the dione (13) containing half a molecule of solvent toluene.

AB - Sodium allyl oxide reacted with 2,3,4,5,6,7,8-heptafluoroquinoline to give allyl 3,4,5,6,7,8-hexafluoroquinolin-2-yl ether (7) and allyl 2,3,5,6,7,8-hexafluoroquinolin-4-yl ether (8) in the ratio 3.4:1 respectively, and with 1,3,4,5,6,7,8-heptafluoroisoquinoline to give allyl 3,4,5,6,7,8-hexafluoroisoquinolin- 1- yl ether (9). Thermolyses of (7) and (9) in tetralin at 212°C gave the Claisen rearrangement products (10) and (12) in which nitrogen is the migration terminus, in slow reactions over 48 h, whereas the isomerisation of (8) to (11) in which carbon is the migration terminus, was complete within 2.5 h at 147.5°C. Compound (11) is very susceptible to hydrolysis, giving with undried toluene, the dione (13) containing half a molecule of solvent toluene.

UR - http://dx.doi.org/10.1016/S0022-1139(00)81077-5

U2 - 10.1016/S0022-1139(00)81077-5

DO - 10.1016/S0022-1139(00)81077-5

M3 - Article

VL - 38

SP - 421

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

IS - 3

ER -