Aziridiniminium salts

Bernard-Henriet, Christiane; HOET, P.; Ghosez, Léon; TOUILLAUX, R.

doi:10.1016/s0040-4039(01)83021-5

Cited by 19 publications

(4 citation statements)

References 7 publications

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“…166 Furthermore, 2-aminoaziridines have also been prepared via stable aziridiniminium salts, obtained by reaction of 2-amino-1-azirines with Ph 3 C + BF 4 -, upon treatment with different types of carbanions. 167…”

Section: C-aminoaziridinesmentioning

confidence: 99%

Synthesis and Reactivity of C-Heteroatom-Substituted Aziridines

2007

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Section: C-aminoaziridinesmentioning

confidence: 99%

Synthesis and Reactivity of C-Heteroatom-Substituted Aziridines

2007

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“…Hatem attributed this change in regioselectivity to a β-substituent effect; that is, a nucleophilic radical preferentially attacks the carbon that is not substituted with the EWG. 164 In 2001, Hatem reported a nBu 3 Sn-radical-initiated tandem addition/cyclization of allenetethered hydrazones and oximes using identical reaction conditions to previous reports. 165 As discussed in Scheme 136, the five-membered ring of 451 arises from attack of the tin radical at C2, followed by 5-exo cyclization of the attack of the resulting nucleophilic carbon radical on the oxime carbon.…”

Section: Tandem Reactions Initiated By Sn Radicalsmentioning

confidence: 86%

Mechanistic Aspects and Synthetic Applications of Radical Additions to Allenes

2019

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More than 50 years have passed since Haszeldine reported the first addition of a trifluoromethyl radical to an allene; in the intervening years, both the chemistry of allenes and the reactivity of single-electron species have become topics of intense interest. In this Review, we provide an overview of the fundamentals of radical additions to allenes and highlight the emergence of theoretical and experimental evidence that reveals unique reactivity patterns for radical additions to allenes as compared with other unsaturated compounds. Factors capable of exerting control over the chemo-, regio-, and stereoselectivities of the attack of carbon-and heteroatom-based radicals at each of the three potential reactive sites in an allene substrate are described. These include reaction conditions, the nature of the attacking radical, the substitution pattern of the allene, and the length of the linker between the radical center and the proximal allene carbon in the substrate. Cycloaddition reactions between allenes and partners containing π-bonds, which are likely to proceed through radical pathways, are presented to highlight their ability to rapidly access complex polycyclic scaffolds. Finally, the synthetic utility of the products arising from these chemistries is described, including their applications to the construction of complex molecules.

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“…Treatment of 2,2‐dimethyl‐3‐phenyl‐2 H ‐azirine with anhydrous perchloric acid and acetone or acetonitrile gives the oxazoline perchlorate and an imidazolinium perchlorate, while the reaction with anilinium perchlorate gives α‐ammonioisobutyrophenone anil perchlorate 91. Likewise, reaction of azirines with trimethylsilyl triflate or trityl tetrafluoroborate92 yield aziridinium salts, which react with nucleophiles to give 2‐aminoaziridines or further open‐chain products.…”

Section: Reactivity Of 2h‐azirinesmentioning

confidence: 99%