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19-4 - 19-21 Syntheses Limited to Primary Amines 921 1...

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Unformatted text preview: 19-21 Syntheses Limited to Primary Amines 921 ' 1.. rearrangement takes place through a much shorter mechanism than the {rearrangement Which stepts) of the Hofmann rearrangement resemble the mgement? genes as the leaving group in the Hofmann reairangement What IS the leaving '- Ihe Camus rearrangement? a mechanism for the following reaction: CH3O CH3 J H H20 | C—C —N3 *6 CeNl‘h I heat I ’ CH3 CH3 'LRY Synthesis of Amines lion (Section 19-19) 0 :N—OH ZNHZ IJ HEN—OH JJ reduction I R—C—R’ T R—C—R’ _—> R—CH_R’ ketone 0r aldehyde oxime 1° amine ago HQN— Jr0H N\OH H2 NH2 Ni ntanone c clo entanone oxime Cyclopent lamine Y P Y amines 1" amine —R” :NHR” IJ R" — NH; JIJJ reduction J R—CgR’ _—)H+ R— C— R’ _—> R—CH—R’ 7 l ketone or aldehyde N—substituted imine 20 amine —Ph NHPh J| Ph— NH2 JJ (])LiAIH4 J CH3— —c— CH3 ‘31—» CH3—C CH3 ——> cm—cn—cn3 (2) H20 . . acetone phenyhsopropylamine -, IniIIES + N 2° amine R_ _R R—N— R JCJ R—NH—R JJ Na(CH3COO)3BH r J ,, R'— R” (2:)4 R'— C—R” ‘——> R —CH—R H . ketone or Caldehyde iminium salt 3" amine C C CH H3 H3 \../ 3 N 0 N 4 H HMCI-Ia)2 Na(CH3COO)3BH ——) (—— _——> H+ cyclohexanone iminium sait- N,N—dimethylcyclehexylamine (Continued) ...
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