- A general, regioselective synthesis of 2-alkylanilines
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Reduction of selected 2,1-benzothiazines with sodium amalgam leads to the formation of 2-alkylanilines in high yield. Since the benzothiazines are ultimately derived from aniline, the process constitutes a general, regioselective functionalization of aniline not readily achieved by other means.
- Harmata,Kahraman
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p. 142 - 144
(2007/10/02)
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- Para-bromination of ortho-alkyl anilines
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A process of selectively preparing p-bromo-o-alkylanilines (e.g. 4-bromo-2-methylaniline) by reacting o-alkylanilines (e.g., 2-methylaniline) with unadsorbed bromine in a solvent selected from the group consisting of an inert di- tri- or tetrahaloaliphatic hydrocarbon (e.g., dichloromethane and dibromomethane), an alkyl nitrile (e.g., acetonitrile) and mixtures thereof.
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- New diamines and a process for their production
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New aminoalkyl anilines having the formula: STR1 wherein k is 0 or 1; QNH2 is a residue of formula STR2 which is situated in one of the positions of the benzene ring ortho or para to the amino group and wherein n is an integer from 1 to 15, R1 is C1 -C8 alkyl, R2 is C1 -C4 alkyl or R1 and R2, together with the carbon atom to which they are attached, form a C5 -C8 cycloalkylene residue, R3 is H or C1 -C6 alkyl, C3 -C8 cycloalkyl, or C6 -C10 aryl; and R4 and R5 are H or C1 -C4 alkyl; as well as the corresponding salts of compounds of formula I with organic or inorganic acids and metal salt complexes; process for their production; and their use as intermediates for polyamides.
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- Photochemical Reaction of Optically Active 2-(1'-Methylallyl)anilines with Methanol
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It is shown that (-)-(S)-2-(1'-methylallyl)aniline ((-)-(S)-4) on irradiation in methanol yields (-)-(2S,3R)-2,3-dimethylindoline ((-)-trans-8), (-)-(1'R,2'R)-2-(2'-methoxy-1'-methylpropylaniline ((-)-erythro-9) as well as racemic (1'RS,2'SR)-2-(2'-methoxy-1'-methylpropyl)aniline ((+/-)-threo-9) in 27.1, 36.4 and 15.7percent yield, respectively (see Scheme 3).By deamination and chemical correlation with (+)-(2R,3R)-3-phenyl-2-butanol ((+)-erythro-13; see Scheme 4) it was found that (-)-erythro-9 has the same absolute configuration and optical purity as the starting material (-)-(S)-4.Comparable results are obtained when (-)-(S)-N-methyl-2-(1'-methylallyl)aniline ((-)-(S)-7) is irradiated in methanol, i.e. the optically active indoline (+)-trans-10 and the methanol addition product (-)-erythro-11 along with its racemic threo-isomer are formed (cf.Scheme 3).These findings demonstrate that the methanol addition products arise from stereospecific, methanol-induced ring opening of intermediate, chiral trans-(->(-)-erythro-compounds) and achiral cis-spiroocta-4,6-dien-8-imines (->(+/-)-threo-compounds; see Schemes 1 and 2).
- Scholl, Bernhard,Hansen, Hans-Juergen
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p. 1823 - 1832
(2007/10/02)
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- N-aryl-N'-(cyclo)-alkyl-thioureas and their use as agents for combating animal pests and plant pests
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N-Aryl-N'-(cyclo)-alkyl-thioureas of the formula STR1 in which R1 represents alkyl-(C1 -C6) or cycloalkyl-(C3 -C7), R2 represents alkyl-(C2 -C6) or cycloalkyl-(C3 -C7), R3 represents alkyl-(C1 -C6), alkenyl-(C3 -C6), cycloalkyl-(C3 -C7), cycloalkenyl-(C5 -C7) or halogen, n represents 0, 1 or 2, and R7 represents optionally substituted cycloalkyl-(C3 -C10), optionally substituted cycloalkenyl-(C5 -C10) or the radical STR2 in which R4 represents hydrogen, alkyl-(C1 -C6) or cycloalkyl-(C3 -C7) and R5 and R6 may be identical or different and represent alkyl-(C1 -C6) or cycloalkyl-(C3 -C7), and acid addition salts thereof, are useful for their ectoparasiticidal, insecticidal, fungicidal and acaricidal effects. These compounds may be produced, inter alia, by reacting aryl isothiocyanates of the formula STR3 with amines of the formula H2 N--R7.
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