Polyfluorinated esters of 4-chloro-2-oxobut-3-ynoic acid. Cycloaddition reactons of hexafluoroisopropyl 4-chloro-2-oxobut-3-ynoate, an incredibly electrophilic alkyne

被引：5
|
作者：
Koldobskii, Andrey B. [1 ]
Shilova, Olga S. [1 ]
Artyushin, Oleg, I [1 ]
Kagramanov, Nicolay D. [1 ]
Moiseev, Sergey K. [1 ]
机构：
[1] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Vavilova Str 28,V-334, Moscow 119991, Russia
来源：
JOURNAL OF FLUORINE CHEMISTRY | 2020年 / 231卷
关键词：
Polyfluoroalkyloxalyl chlorides; Acylation; Chlorination; Cycloaddition reactions;
D O I：
10.1016/j.jfluchem.2020.109463
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
A series of chloroalkynes activated with extremely strong electron withdrawing polyfluoroalkyloxalyl substituents were prepared for the first time from available bis(trimethylstannyl) acetylene and the corresponding acid chlorides. Hexafluoroisopropyl ester, thus obtained, probably proved to be the most electrophilic alkyne known so far. It is not only extremely strong dienophile in the Diels-Alder reaction, but undergoes the unusual uncatalyzed [2 + 2]-cycloaddition reactions with simple alkenes under very mild conditions.
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页数：9
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