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By O. C. Dermer

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Extra resources for Ethylenimine and Other Aziridines. Chemistry and Applications

Sample text

It has been obtained by the Wenker method (202,1513,1765), as has l-amino-2-phenylaziridine in 6 0 - 7 0 % yield from the dimesyl ester of 1-phenyl-1,2-ethanediol and hydrazine (1284c). An old observation that dibromides of 2-bromoanethole and 2,x-dibromoanethole with excess aniline yield products that probably have the aziridine structure is also to be cited (1676), but should be confirmed. Less acceptable are the aziridine structures attributed to the products of reaction of potassium anilide with the dibromides of oleic and ricinoleic acids (1757a), which are not classified as aziridines in Beilstein and need reinvestigation.

P. p. 100 25 90-100 — 45 40 120 — 240 120 270 10 60 300 (3 days ) 540 — c k c 100 0* 0 92 44 85 — 17" 90 56 61 c,h 60-66 79 551 252 551 250 247 251 251 1467 1467 47a, 1467 2538a 253 253 722b 1 J 1 h 0 f e d c b Th e á-glucosid e was used unles s otherwis e noted . Th e acylamin o substituen t is understoo d t o be on a deoxy carbo n atom , an d a 4,6-benzyliden e grou p presen t unles s otherwis e noted . As th e free epimine . TH F = tetrahydrofuran . N o benzyliden e grou p present . Of th e benzylidenebis(aziridine) .

I I J + + L+H I I R R 35 (26) While 1-acylaziridines can be rearranged to oxazolines (1656), it is not likely that oxazoline formation proceeds by way of aziridine intermediates as a INTRAMOLECULA R DISPLACEMEN T BY AMIDE ANIONS 53 rule (1667). Those few instances in which aziridines are formed rather than oxazolines will now be discussed. Possibly because of decreased resonance stabilization of the anion 36 resulting from removal of a proton from a mono-7V-substituted urethan (Eq 27), stron g bas e RNHC0 R ' 2 • - RNC0 R ' (27) 2 36 which is apparently less than for other carboxamide anions, internal displacement of halide by the amide nitrogen atom to give aziridines occurs (Eq 28) instead of the displacement by amide oxygen to give oxazolines (Table 1-VIII).

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