By Stuart Spicer
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R N (XI, - -H 'R N (X)n T-7 N I R (87) The latter approach, best exemplified by triazoline formation and decomposition, is discussed first. A. Aziridine Synthesis via Triazolines The formation of aziridines from triazolines (Eq. 88) is not a new reaction. Originally the conversion was accomplished under thermal (usually > 100") conditions. Side reactions include imine formation (Eq. 89), isomerization of the triazoline before decomposition (Eq. 90),"'** 9I' isomerization of the aziridine once formed (Eq.
B-Al-H 'OH N H c6HUR C,H,CCH,R I1 N 'OH (82) i-BuMgBr I R = CH, (65%) R = C,H, (6046) C6H5CH2C i P r II N 'OH i-BuMgBi 40% H c6Hwp N (83) I H LiAM, N I H (84) TABLE 31. AZIRIDINES VIA UAIH, REDUCTION OF OXIMES~ I H R’ R’ Yield (%I Ref. PclOH, Pc lOH,CH I CbHS CH, H C2HS CbHSCH2 ‘bHS 25 7 24 77 25 22 17 11 16 3; 34 64 16 40 300 300 300 300 300 300 300 300 300 300 300 300 ‘bHS ‘bH5 CSHJ 6 ‘ CbHS w c 6H4 flH30C6H4 6 ‘ HS &,OH, BC’OH, C,HSCHCCH3 HS H H H CH3 H H H 245 a Wavy lines indicates the new N-C bond.
H/C'Hs + - 'fwc? N R = CH, (80%) R = C,H, (100%) R = C,H, (100%) RMgX (56) N A I H H The generality of this reaction is indicated in Table 23. Aldol-type condensations have also been reported (Eqs. C:H, + ' Br I C4-t R' R' R3 Yield (96) Cycloadditions to azirines also yield aziridines. @-2m 78 Photolysis of a variety of azirines (Eq. 62) has been shown to yield products of structures 79 and 80. Apparently the azirine undergoes photochemical ring opening to a nitrile ylid which, in turn, undergoes (thermal) IJ-dipolar cycloaddition to a second molecule of azirine (Eq.