Aziridine → HCID 86706739, compound

HRID 2170133Notes

Reaction equation

HRID 2170133 reaction equation
N1C[CH2:2]1.C1(C)C=CC(N=[N+]=[N-])=CC=1.C=CCCCCCCCC.[CH3:24][C:25]12[N:31]([C:32]3[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=3)[CH:30]1[CH2:29]CC[CH2:26]2.CC1CCCCC=1>>[CH3:26][C:25]1([CH3:24])[C:30]([CH3:29])([CH3:2])[N:31]1[C:32]1[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=1

Participants

6

Reactant 5

HCID 9033AziridineHCID 115741-MethylcyclohexeneHCID 133811-DeceneHCID 1374301-Azido-4-methylbenzene2×HCID 86706738HCID 86706738, compound

Product 1

HCID 86706739HCID 86706739, compound

Procedure

Selected control reactions following the method of the General Catalytic Reaction were attempted but without [(Me,EtTCPh)Fe(NCCH3)2](PF6)2. These reactions either gave lower yields for aziridines or almost no isolable aziridine. Two example cases are shown. 2-octyl-1-(ptolyl)aziridine. p-Tolyl azide (0.096 g, 0.72 mmol) and 1-decene (1.853 g, 13.2 mmol) were used in the General Catalytic Reaction described above yielding 0.078 g, 43% yield. 1-methyl-7-(p-tolyl)-7-azabicyclo[4.1.0]heptane. p-Tolyl azide (0.203 g, 1.53 mmol) and 1-methylcyclohexene (4.055 g, 42.2 mol) were used in the General Catalytic Reaction described above yielding 0.007 g, 2% yield.

Workup

  1. customabove yielding 0.078 g, 43% yield
  2. customabove yielding 0.007 g, 2% yield

Sources & evidence

ORD record
ord-17c4eac939194278a5143ff1429c6480
Source dataset
uspto-grants-2015_06
Patent number
US09050589B2

Reaction notes

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