[2 + 1] Cycloaddition Reaction of Dialkylthioketenes with Carbenes – Isomerization of the Resulting Alkylidenethiiranes | Zendy

Behr Helmut | Zendy; Bolte Oliver | Zendy; Dräger Gerald | Zendy; Ries Monika | Zendy; Schaumann Ernst | Zendy

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[2 + 1] Cycloaddition Reaction of Dialkylthioketenes with Carbenes – Isomerization of the Resulting Alkylidenethiiranes

Author(s) -

Behr Helmut,

Bolte Oliver,

Dräger Gerald,

Ries Monika,

Schaumann Ernst

Publication year - 1996

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199619960809

Subject(s) - chemistry , isomerization , cycloaddition , diazo , decomposition , medicinal chemistry , photochemistry , catalysis , stereochemistry , organic chemistry

Carbenes generated by metal‐catalyzed decomposition of diazo compounds 2 undergo a smooth cycloaddition to the CS bond of thioketenes 1 ; products 3 were characterized by spectroscopic means as well as an X‐ray structural investigation of 3b . However, photolytic generation of diphenylcarbene from diphenylketene led to an isomeric alkylidenethiirane 4a in the reaction with di‐ tert ‐butylthioketene ( 1a ). Analogously, alkylidenethiiranes 3a, b, d, g, h could be photoisomerized to isomers 4a, b, d, g, h . The corresponding rearrangement of S ‐oxides 8 afforded isomers 9 .

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