Acenaphthylene → 1-Methylthioacenaphthylene

HRID 2302122Notes

Reaction equation

HRID 2302122 reaction equation
[CH3:1][S:2]SC.[CH:5]1[C:15]2=[C:16]3[C:11](=[CH:12][CH:13]=[CH:14]2)[CH:10]=[CH:9][CH:8]=[C:7]3[CH:6]=1>N1C=CC=CC=1>[CH3:1][S:2][C:6]1[C:7]2=[C:16]3[C:11](=[CH:10][CH:9]=[CH:8]2)[CH:12]=[CH:13][CH:14]=[C:15]3[CH:5]=1

Participants

4

Reactant 2

HCID 9161AcenaphthyleneHCID 12232Dimethyl Disulfide

Product 1

HCID 109104981-MethylthioacenaphthyleneYield 76%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

As an example of the benefits that can be realized by use of the two-step procedure, controlled potential electrolysis of dimethyl disulfide in the presence of acenaphthylene in the absence of an organic nucleophilic base resulted in copious polymer formation. But when the same electrolysis procedure was conducted in the additional presence of pyridine, an oxidation-resistant adduct of this invention formed which on eliminative aromatization in the second step resulted in the production of 1-methylthioacenaphthylene in 76% yield using electrochemical reductive elimination.

Workup

  1. customresulted in copious polymer formation
  2. customan oxidation-resistant adduct of this invention formed which on eliminative aromatization in the second step

Sources & evidence

ORD record
ord-a1736e7a654148eb9171388fc5a46d30
Source dataset
uspto-grants-2002_08
Patent number
US06432294B1

Reaction notes

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