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Rearrangements of 2‐ and 3‐Furfurylidene
Author(s) -
Albers Reinhard,
Sander Wolfram
Publication year - 1997
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.199719970518
Subject(s) - chemistry , diazo , photodissociation , carbene , matrix isolation , methane , thermochemistry , pyrolysis , ketene , cyclopropene , photochemistry , medicinal chemistry , organic chemistry , catalysis , molecule
The photo‐ and thermochemistry of diazo(2‐furyl)methane ( 3 ) and diazo(3‐furyl)methane ( 6 ) was investigated using the matrix isolation technique. Photolysis of 3 results in the formation of ( Z )‐pent‐2‐en‐4‐yn‐1‐al ( 2 ) in a clean reaction, in agreement with the observation of Shechter et al. Photolysis or pyrolysis of diazo compound 6 yields ( s‐Z )‐(α‐formyl)methylenecyclopropene ( s‐Z ‐ 13 ) as the only detectable product. Carbene 14 and cyclopropene 15 are proposed as intermediates, but not stable under the reaction conditions and thus not directly observed. The reaction sequence 6→13 provides a novel and simple route to methylenecyclopropenes.