Chapter I Aziridines (pages 1–214): James A. Deyrup
Chapter II Azirines (pages 215–332): Vasu Nair
Chapter III Three?Membered earrings Containing Sulfur (pages 333–629): Uri Zoller
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Additional resources for Chemistry of Heterocyclic Compounds: Small Ring heterocycles, Part 1: Aziridines, Azirines, Thiiranes, Thiirenes, Volume 42
The heterocyclic precursors appears to offer no advantages over the oximes (Table 35). Aziridines 48 & R N LiAlH,+ H /H N -. 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.
M The same reagent has been used to reduce hydrazone salts as shown in Table 34"5 Certain Grignard reagents also result in reduction,= as indicated in Eqs. 82 and 83. The LiA& reduction of 2-isoxazolines also produces aziridines (Eq. 307* The mechanism is unproved but undoubtedly resembles the oxime reductions. The heterocyclic precursors appears to offer no advantages over the oximes (Table 35). Aziridines 48 & R N LiAlH,+ H /H N -. 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.
In these cases (Tables 16 and 17) azirine intermediates seem much less likely. TABLE 14. AZIRIDINES FROM LiAIH, REDUCTIONS OF NITRILE DERIVATIVES R1 R’ X Yield (%I Ref. G H , i€,H, H H H H H c1 c1 82 72 67 CI 58 H c1 c1 46 68 83 198 198 198 198 198 199 200 H 0 Ts 54 20 1 nC6H13 6 ‘ ScHZ C,H, C6Hll (CH,)s a a AZIRIDINES FROM LiAlH, REDUCTIONS OF NITRILE DERIVATIVESa TABLE IS. -201 33%’0’ 72%’” Wavy line indicates the new C-N bond. +C=N-R’ and X I H R‘ R’ RI-+C=N- X TABLE 16. R1 t-:p F:p R’ I AZIRIDINES FROM a-HALOIMINE REDUCTIONS WITH LiAIH, R’ C*H, H H H H H i-Pr H r-B u H CH3 CH 3 CH3 CH3 CH, CH 3 CH3 CH3 C,H’ C’H’ (CH,), (CHI), CH3 CH, X R3 Yield (%) Ref.