Observations on the synthesis of functionalised methyleneaziridines

J  Ince; T M  Ross; M  Shipman; A M Z  Slawin; D S  Ennis

Observations on the synthesis of functionalised methyleneaziridines

J Ince, T M Ross, M Shipman, A M Z Slawin, D S Ennis

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Abstract

N-Triphenylmethyl-2-methyleneaziridine 8 was synthesised from N-(2-bromo-2-propenyl)-amine 7 by treatment with sodium amide in liquid ammonia and its structure established using x-ray crystallography. Using modified conditions, (S)-N-(1-phenylethyl)-2-methyleneaziridine 9 was prepared in enantiomerically enriched form. Studies directed towards the synthesis of N-tosyl and N-Boc methyleneaziridines 14 and 15 respectively reveal limitations with this methodology. Copyright (C) 1996 Elsevier Science Ltd

Original language	English
Pages (from-to)	7037-7044
Number of pages	8
Journal	Tetrahedron
Volume	52
Issue number	20
Publication status	Published - 13 May 1996

Cite this

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title = "Observations on the synthesis of functionalised methyleneaziridines",

abstract = "N-Triphenylmethyl-2-methyleneaziridine 8 was synthesised from N-(2-bromo-2-propenyl)-amine 7 by treatment with sodium amide in liquid ammonia and its structure established using x-ray crystallography. Using modified conditions, (S)-N-(1-phenylethyl)-2-methyleneaziridine 9 was prepared in enantiomerically enriched form. Studies directed towards the synthesis of N-tosyl and N-Boc methyleneaziridines 14 and 15 respectively reveal limitations with this methodology. Copyright (C) 1996 Elsevier Science Ltd",

author = "J Ince and Ross, {T M} and M Shipman and Slawin, {A M Z} and Ennis, {D S}",

year = "1996",

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pages = "7037--7044",

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T1 - Observations on the synthesis of functionalised methyleneaziridines

AU - Ince, J

AU - Ross, T M

AU - Shipman, M

AU - Slawin, A M Z

AU - Ennis, D S

PY - 1996/5/13

Y1 - 1996/5/13

N2 - N-Triphenylmethyl-2-methyleneaziridine 8 was synthesised from N-(2-bromo-2-propenyl)-amine 7 by treatment with sodium amide in liquid ammonia and its structure established using x-ray crystallography. Using modified conditions, (S)-N-(1-phenylethyl)-2-methyleneaziridine 9 was prepared in enantiomerically enriched form. Studies directed towards the synthesis of N-tosyl and N-Boc methyleneaziridines 14 and 15 respectively reveal limitations with this methodology. Copyright (C) 1996 Elsevier Science Ltd

AB - N-Triphenylmethyl-2-methyleneaziridine 8 was synthesised from N-(2-bromo-2-propenyl)-amine 7 by treatment with sodium amide in liquid ammonia and its structure established using x-ray crystallography. Using modified conditions, (S)-N-(1-phenylethyl)-2-methyleneaziridine 9 was prepared in enantiomerically enriched form. Studies directed towards the synthesis of N-tosyl and N-Boc methyleneaziridines 14 and 15 respectively reveal limitations with this methodology. Copyright (C) 1996 Elsevier Science Ltd

M3 - Article

SN - 0040-4020

VL - 52

SP - 7037

EP - 7044

JO - Tetrahedron

JF - Tetrahedron

IS - 20

ER -

Observations on the synthesis of functionalised methyleneaziridines

Abstract

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