The first general and efficient method for the synthesis of tertiary alkyl fluorides

“…18% yield. 72 Alternatively, Bu 3 SnCH 2 CH 2 CN can be used as the source of the CH 2 CH 2 CN group. 72 Similarly, α-bromo-α-fluoroesters can also be utilized in the synthesis of γ-fluoronitriles (Scheme 51).…”

Section: Syntheses Of Ethyl α-Fluorocyanoacetate and Its Derivativesmentioning

confidence: 99%

Chemistry of fluoroalkyl cyanides

Usachev¹

2020

Arkivoc

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This review is devoted to the chemistry of fluoroalkyl cyanides (R F -nitriles): their synthesis and chemical properties. Syntheses of non-functionalized R F -nitriles (FCH 2 CN, F 2 CHCN, CF 3 CN, C 2 F 5 CN, FCH 2 CH 2 CN, etc.) and dinitriles (NCCHFCN, NCCF 2 CN, NCCF 2 CF 2 CN, etc.) are considered. The synthesis of functionalized R F -nitriles such as F 2 NCF 2 CN, F 2 NCClFCN, Cl 2 CFCN, Br 2 CFCN, (O 2 N) 2 CFCN, O 2 NCF 2 CH 2 CH 2 CN, and dinitriles, such as O(CF 2 CN) 2 , NCCF 2 N=NCF 2 CN, is also considered. R F -Nitriles are attractive electrophilic, enophilic, and dienophilic building-blocks: they were used in the synthesis of various fluorine-containing heterocyclic compounds, such as R F -bearing pyridines, 1,3,5-triazines, tetrazoles, and others. R F -nitriles were also used in the synthesis of unusual acyclic compounds, such as fluoroalkylated N,N-difluoroamines, F 2 NCF 2 CF 2 N=SF 2 , R Fimino esters, and others.

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“…TPP-NH 2 was obtained as a dark purple solid (233 mg, 0.370 mmol, 96 %). 1 Ethyl 3-oxoindane-5-carboxylate 5: [43] To a solution of 3-oxoindane-5-carboxylic acid (1.00 g, 5.68 mmol) in ethanol (100 mL) concentrated 12 M HCl (0.47 mL) was added. The reaction mixture was heated to reflux and left to stir overnight.…”

Section: Computational Detailsmentioning

confidence: 99%

Exciton‐Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host−Guest Complexes with a Bis(zinc porphyrin) Tweezer

et al. 2018

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A stiff-stilbene-linked bisporphyrin tweezer with inherent helicity was used for exciton-coupled circular dichroism (ECCD) characterization of a series of monotopically binding amine guest molecules. CD signals were observed for a variety of monoamines at relatively low tweezer/amine (host/guest) ratios between 1 : 10 to 1 : 70. For the amines producing the most intense CD signals, a binding stoichiometry of 1 : 2 was found. A likely explanation is the presence of guest-guest interactions in the complexes. This is supported by the correlation observed between CD signal intensity and magnitude of possible noncovalent binding between the guests, which can be divided into three groups showing no, moderate and strong response, respectively. Further support for this rationalization comes from molecular modelling.

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The first general and efficient method for the synthesis of tertiary alkyl fluorides

Cited by 19 publications

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Ethyl dibromofluoroacetate: a versatile reagent for the synthesis of fluorinated molecules

Ethyl dibromofluoroacetate: a versatile reagent for the synthesis of fluorinated molecules

Chemistry of fluoroalkyl cyanides

Exciton‐Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host−Guest Complexes with a Bis(zinc porphyrin) Tweezer

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