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One‐Pot Synthesis of Lactams from Cycloalkanes and tert ‐Butyl Nitrite by Using N ‐Hydroxyphthalimide as Key Catalyst
Author(s) -
Hashimoto Masaharu,
Sakaguchi Satoshi,
Ishii Yasutaka
Publication year - 2006
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200600187
Subject(s) - triethylamine , catalysis , chemistry , caprolactam , cyanuric chloride , cyclohexane , beckmann rearrangement , organic chemistry , solvent , chloride , salt (chemistry) , medicinal chemistry
Lactams were successfully synthesized in the one‐pot reaction of cycloalkanes and t BuONO in the presence of N ‐hydroxyphthalimide as a key catalyst. Cyclododecane and cyclohexane were treated with t BuONO followed by triethylamine and then cyanuric chloride in a one‐pot manner to give laurolactam and ε‐caprolactam, respectively, in good yields. The Beckmann rearrangement of oximes by cyanuric chloride was found to be accelerated by the use of 1,1,1,3,3,3‐hexafluoro‐2‐propanol as solvent. The method provides the first successful environmentally benign direct synthetic route to lactams from cycloalkanes without the formation of any salt.