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Homocub‐1(9)‐ene trapped
Author(s) -
Chen Ning,
Jones Maitland
Publication year - 1988
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610010509
Subject(s) - chemistry , flash vacuum pyrolysis , ene reaction , hydrazone , indene , decomposition , pyrolysis , tosyl , organic chemistry , photochemistry , medicinal chemistry
Decomposition of the tosylhydrazone salts formed from cubyl carboxaldehyde and homocubanone, potential precursors of cubylcarbene ( 5 ) and homocubanylidene ( 6 ), leads in each case to products derived from 6 . It is suggested that homocub‐1(9)‐ene ( 7 ) is the active ingredient in the formation of 6 from both precursors. The hydrazones formed from N ‐aziridylamines are useful photochemical sources of 6 , and presumably other carbenes. Flash vacuum pyrolysis of the tosyl hydrazone salts and hydrazones at 600°C leads to indene.