Novel epoxide formation in the reaction of 2-bromo-3-methyl-1,4-naphthoquinone with 1,3-propanedithiol.
A novel epoxide 2 was formed as the major product in the reaction of 2-bromo-3-methyl-1,4-naphthoquinone with 1,3-propanedithiol in the presence of triethylamine in 92% yield. Molecular oxygen is suggested to be the source of the added oxygen in 2, an oxidation product of its precursor 3. A strong base such as triethylamine is required to abstract the methyl hydrogen of 1,4-naphthoquinones, leading to the formation of 3 as well as 2.
Department of Chemistry, Occidental College, Los Angeles, CA 90041, USA.
Tom M
TM
Lam
Chain
C
Lee
Katherine
K
Katardjieff
Tetsuo
T
Otsuki
D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D008968:Molecular Conformation; D009285:Naphthoquinones / Q000737:chemistry*; D011407:Propane / Q000031:analogs & derivatives* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*
C556339:2-bromo-3-methyl-1,4-naphthoquinone; D004852:Epoxy Compounds; D009285:Naphthoquinones; D013438:Sulfhydryl Compounds; C508630:1,3-propanedithiol; D011407:Propane