By O. C. Dermer
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Extra resources for Ethylenimine and Other Aziridines. Chemistry and Applications
As th e free epimine . TH F = tetrahydrofuran . N o benzyliden e grou p present . Of th e benzylidenebis(aziridine) . Along with 25 % of th e oxazoline . Oxazolin e also formed . In othe r cases, not cited here , th e â-hexos e derivativ e gave only th e oxazoline , etc. No benzyliden e grou p present , bu t a 5-mesyl was. * Th e 5-Ms grou p was displace d by th e 5-Bz grou p in th e product . No benzyliden e grou p present , bu t a 5-azid o grou p was. Th e produc t was isolate d as th e dibenzoy l derivative .
9 ÷ 1 0 s e c . b c 5 1 d e f - 5 - 5 -1 - 5 -1 -1 9 h - 5 -1 + In contrast, B z N H C H M e C H P h S M e I " gives only the oxazoline (3465). 1]octan-e«ifo-7-ol tosylate are best explained by postulating the acylaziridinium ion 3 8 as an intermediate (1792). 2 CH P h 2 Desire for possible antitumor drugs and intermediates for synthesis of various amino sugars has motivated related research. 1 eq. 1JV NaOM e or NaOH , resp . 6N Mixed ales. p. p. p. p. p. , resp . p. p. p. 100 25 (°Q Temp . Reactio n condition s PREPARATIO N OF 2,3-EPIMIN O SUGAR DERIVATIVE S Tabl e 1-IX c c c c 32 38 56 * 49* 78 / 61 68-73 — 60 Few 120 45 30 120 60 — 88-90 — 65 29 72 53 53 76 85 Yield (% ) — 4-5 90 30 180 20 1080 10 Few Tim e (min.
0 NC H ) 6 2 4 6 4 2-(p-0 NC H CO)-3-P h 1,3-Me -2-(^-PhC H CO ) 2,3-Bz -l-M e 2 6 4 2 6 4 2 l-Me-3-Ph-2-(^-MeC H CO ) 6 4 2,3-Bza-l-E t 1-c-QH i -2-(;7-PhC H CO ) 2-Bz-l-c-C H -3-P h 1 6 6 4 n 2-Bz-l-c-C H -3-(/7-MeOC H ) 2-Bz-l-c-C H -3-(/7-0 NC H ) 2-Bz-l-c-QH ! 6 43 50 40 High — 80 — 78 46 50-54 — 97-100 — 89 60-90 » 68 65 43 INTRAMOLECULA R DISPLACEMEN T BY TH E AMIN O GROU P Tabl e 1-V—continue d Aziridin e made , or substituent s therei n Method " % Yield" Reference s Aziridines Containing No Functional Groups—continued 2-Bz-l-PhCH -3-P h 2 2-Bz-l-PhCH -3-(m-0 NC H ) l-c-C H -3-Me-2-(p-PhC H CO ) l-c-C H !