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Mass Spectra of 2‐ and 6‐Substituted‐3‐Pyrones: Competition Between “RETRO‐DIELS‐ALDER” Fragmentation and Substituent Loss
Author(s) -
Lin ShawTao,
Kuo YuehHsing,
Lee MingShi
Publication year - 1988
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.198800053
Subject(s) - chemistry , substituent , fragmentation (computing) , mass spectrum , computational chemistry , diels–alder reaction , medicinal chemistry , photochemistry , cleavage (geology) , stereochemistry , organic chemistry , catalysis , ion , geotechnical engineering , fracture (geology) , computer science , engineering , operating system
The mass spectra of a series of 6‐hydroxy‐3‐pyrones and their derivatives showed a marked dependence upon the nature of the substituent. The “retro‐Diels‐Alder” reaction is the primary decomposition observed for the parent compounds, while the α‐cleavage (substituent loss) competes with the “retro‐Diels‐Alder” reaction for their derivatives. An interpretation of this difference based on the charge location and the thermochemical data is proposed.