Novel ring opening reactions of methyleneaziridines

Ince, Julie; Shipman, Michael; Ennis, David S.

doi:10.1016/s0040-4039(97)01311-7

Cited by 18 publications

(2 citation statements)

References 10 publications

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“…path a). 20,49 However, in the MCR, where copper(I) salts are present, we felt that 'conjugate-type' opening could not be readily discounted (path b).…”

Section: Scheme 14 Solid-phase Ketone Mcrmentioning

confidence: 99%

Methyleneaziridines: Unusual Vehicles for Organic Synthesis

Shipman¹

2006

Synlett

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“…path a). 20,49 However, in the MCR, where copper(I) salts are present, we felt that 'conjugate-type' opening could not be readily discounted (path b).…”

Section: Scheme 14 Solid-phase Ketone Mcrmentioning

confidence: 99%

Methyleneaziridines: Unusual Vehicles for Organic Synthesis

Shipman¹

2006

Synlett

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“…14 In this paper, we disclose studies from our laboratories which establish that methyleneaziridines can be induced to undergo smooth nucleophilic ring opening reactions in the presence of a variety of alkyl chloroformates and acid chlorides under relatively mild reaction conditions and provide some mechanistic insights into the ring opening reactions of 2-methyleneaziridines. 15…”

Section: Introductionmentioning

confidence: 99%

Observations on the ring opening reactions of 2-methyleneaziridines with acid chlorides and alkyl chloroformates

Ennis

Ince

Rahman

et al. 2000

J. Chem. Soc., Perkin Trans. 1

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A variety of 1-alkyl-2-methyleneaziridines react with alkyl chloroformates (MeO 2 CCl, PhCH 2 O 2 CCl) or acid chlorides (AcCl, p-NO 2 C 6 H 4 COCl) at room temperature in nonpolar solvents (CH 2 Cl 2 , THF, toluene) to produce ring opened enamide products in moderate to good yields. Mechanistic studies using 3-deuterio-N-(1-phenylethyl)-2-methyleneaziridine suggest the reactions proceed by initial N-acylation to form the corresponding aziridinium cation (e.g. 27) which subsequently undergoes regiospecific ring opening by chloride ion at the sp 3 hybridised aziridine carbon atom to produce the observed products.

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Methyl Chloroformate

Sampson¹,

Ragan²

2009

Encyclopedia of Reagents for Organic Synthesis

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Novel ring opening reactions of methyleneaziridines

Cited by 18 publications

References 10 publications

Methyleneaziridines: Unusual Vehicles for Organic Synthesis

Methyleneaziridines: Unusual Vehicles for Organic Synthesis

Observations on the ring opening reactions of 2-methyleneaziridines with acid chlorides and alkyl chloroformates

Methyl Chloroformate

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