By H Suschitzky; O Meth-Cohn; G V Boyd
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Extra resources for Heterocyclic Chemistry Vol. 2 A review of the literature abstracted between July 1979 and June 1980
OMe Formation of Other Ring Systems from Aziridines. The aziridines (262; R' = Ph, 4-C1C6H4, or 4-MeC6H4) reacted with R2NC (R2 = Pr', Ph, But, or Bu'CH2CMe,) in CH2C12to give the azetidines (263; R' = phthalimido) (404 9 ' / 0 ) . ~The ~ ~ azetidines subsequently yielded acyclic imines after rearrangement. NRL (263) CONHR (264) CONHR (265) An improved synthesis of the pyrrolidinones (265; R = Ph, 4-C1C6H4, 3,4CI2C6H3, 1-naphthyl, or Et) from (264) involves their reaction with excess NaCH(CO,Et), in the absence of 205 206 207 M.
C. Van de Sande, Z. S. Ahmad, F. Borchers, and K. Levson, Org. , 1978,13,666. r. 7 kJ mol-'. -Photochemical and Thermal. lR9 A theoretical ub initio SCF-CI approach has been used in an investigation of the photochemical behaviour of a z i r i d i n e ~ . ~ ~ ~ ) It has been suggested that, in the gas phase, fission of C-N bonds is favoured whereas C-C bond fission competes in protic solvents. 192This pathway was confirmed by the thermolysis of (236) at 80 OC, which gave (234) (75%). CH=NX (233) X = NHTs (234) (235) Ph (236) X = Nf 'Ph A number of tricyclic aziridines (237; R = H, Me02C, or CN) underwent thermolysis to (239) at temperatures between 80 and 18OoC, the higher The ~ temperature being required for electron-withdrawing ~ u b s t i t u e n t s .
G. "' CI )=CHCH,Li Me Me RZ + RIRZCO -+ R i v ~ H = ~ ~ , 0 (49) (48) (50) Synthesis of Chiral Oxirans. e. it excludes syntheses that rely on the resolution of racemic epoxides). 's of around 30% [all of ( R ) configuration] in PhNO, at 20 "C. The dioxolan (R)( 5 2 ; X = tosyloxy), obtained from di-isopropylidenemannitol, undergoes substitution reactions with CuI plus XLi (X = Me or Bu) Sequential ~ treatment of to yield ( S ) - ( S 2 ; X = Me) and ( S ) - ( 5 2 ; X = B u ) . ~ this dioxolan with HBr and HOAc (to form the bromoacetate) and then Me(CH2)40K and Me(CH,),OH gave samples of the 6)-alkyl-oxirans (53; R' = H, R2 = CH,Me) and (53; R' = H, R' = CH2Bu)with high optical purity.