Unprecedented 1,3-tert-butyl migration via the C–N single bond scission of isonitrile: an expedient metal-free route to N-sulfonyl amidines

2020 ◽  
Vol 56 (60) ◽  
pp. 8408-8411
Author(s):  
Debashish Mishra ◽  
Arun Jyoti Borah ◽  
Pinakinee Phukan ◽  
Debojit Hazarika ◽  
Prodeep Phukan
Keyword(s):  
Alkyl Group ◽  
Single Bond ◽  
Metal Free ◽  
Tert Butyl ◽  
Bond Scission ◽  
And Migration

Treatment of tert-butyl isonitrile with ArSO2NBr2 and nitrile led to simultaneous C–N single bond scission of isonitrile and migration of tert-alkyl group to nitrogen centre of the nitrile precursor, resulting in the formation of N-sufonyl amidine.

A Three Component Iodine-Catalyzed Oxidative Coupling Reaction: A Heterodifunction of 3-Methylindole

2021 ◽  
Author(s):  
Wei Zhang ◽  
Shiqun Xiang ◽  
Weibin Fan ◽  
Jiang Jin ◽  
Yinghua Li ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Peroxy Radicals ◽  
Metal Free ◽  
Tert Butyl ◽  
Oxidative Coupling Reaction

A metal-free synthesis of heterodifunctional indole derivaties is developed through TBHP/KI-mediated oxidative coupling. The reaction constructs C-O and C-C bonds in succession with the help of tert-butyl peroxy radicals generated...

An Efficient Substrate-Induced Method for the Synthesis of CF3-Substituted Cyclopropanes by Metal-Free Reaction of Trifluoromethyl Styrylisoxazoles with Nitromethane

Synthesis ◽  
2020 ◽  
Author(s):  
Feng Li ◽  
Hai Ma ◽  
Qing-he Zhao ◽  
Guang-hao Yu ◽  
Ye-chen Meng ◽  
...  
Keyword(s):  
Functional Groups ◽  
Phase Transfer ◽  
Cyclization Reaction ◽  
Metal Free ◽  
Tert Butyl ◽  
Pharmacological Interest ◽  
Substituted Cyclopropanes

AbstractA series of (trifluoromethyl)cyclopropanes (TFCPs) tolerating a broad range of functional groups, known as tert-butyl bioisosteres, have been obtained from the cyclization reaction between nitromethane­ and 5-[β-(trifluoromethyl)styryl]isoxazoles in 70–94% yields and 75:25 to 90:10 dr. This method offers practical access to this cyclopropyl moiety of pharmacological interest, employing an inorganic base under phase-transfer conditions.

13C lithiation shifts in aldimines and ketimines. Evidence on the configuration of lithiated N-tert-butylimines

1981 ◽  
Vol 59 (20) ◽  
pp. 3007-3011 ◽  
Author(s):  
Robert R. Fraser ◽  
Noemi Chuaqui-Offermanns
Keyword(s):  
Alkyl Group ◽  
Tert Butyl

The 13C shieldings for a series of aldimines and ketimines have been measured along with the shifts for their 1-lithio derivatives. For those aldimines with a primary or secondary alkyl group attached to nitrogen, the "lithiation shifts" for the attached carbon (C-4) were all upfield due to the change from anti to syn configuration on lithiation. In the ketimines and in the N-tert-butyl aldimines and ketimines, the lithiation shifts for the C-4 carbon failed to provide stereochemical information. The shifts at C-1 and C-2 proved similar to those previously observed for lithiated alkenes.

The Mechanism of Hydrocarbon Oxygenate Reforming: CC Bond Scission, Carbon Formation, and Noble-Metal-Free Oxide Catalysts

ChemSusChem ◽  
2013 ◽  
Vol 7 (1) ◽  
pp. 77-81 ◽  
Author(s):  
Yaroslava Lykhach ◽  
Armin Neitzel ◽  
Klára Ševčíková ◽  
Viktor Johánek ◽  
Nataliya Tsud ◽  
...  
Keyword(s):  
Noble Metal ◽  
Oxide Catalysts ◽  
Carbon Formation ◽  
Metal Free ◽  
Bond Scission
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