By Gwynn P. Ellis
Chapter I Chromenes, Chromanones, and Chromones—Introduction (pages 1–10): G. P. Ellis
Chapter II 2H? and 4H?1?Benzopyrans (pages 11–139): E. E. Schweizer and Deborah Meeder?Nycz
Chapter III 3?Chromanols and 4?Chromanols (pages 141–192): I. M. Lockhart
Chapter IV 3?Chromanones (pages 193–206): I. M. Lockhart
Chapter V 4?Chromanones (pages 207–428): I. M. Lockhart
Chapter VI 2,4?Chromandiones and 2,3,4?Chromantriones (pages 429–453): I. M. Lockhart
Chapter VII certainly happening Chromones (pages 455–480): G. P. Ellis
Chapter VIII Analytical features of Chromones (pages 481–494): G. P. Ellis
Chapter IX basic tools of getting ready Chromones (pages 495–555): G. P. Ellis
Chapter X Chromone and its Benzo Derivatives (pages 557–580): G. P. Ellis
Chapter XI Alkylchromones (pages 581–631): G. P. Ellis
Chapter XII Hydroxychromones (pages 633–689): G. P. Ellis
Chapter XIII Alkoxychromones (pages 691–748): G. P. Ellis
Chapter XIV Halochromones (pages 749–779): G. P. Ellis
Chapter XV Nitrochromones (pages 781–798): G. P. Ellis
Chapter XVI Aminochromones (pages 799–854): G. P. Ellis
Chapter XVII Ketonic Chromones (pages 855–901): G. P. Ellis
Chapter XVIII Chromone Carbonitriles and Tetrazole Derivatives (pages 903–920): G. P. Ellis
Chapter XIX Chromone Carboxaldehydes (pages 921–942): G. P. Ellis
Chapter XX Chromone Carboxylic Acids and Their Derivatives (pages 943–1042): G. P. Ellis
Chapter XXI Bischromones and Bichromones (pages 1043–1083): G. P. Ellis
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Additional info for Chemistry of Heterocyclic Compounds: Chromenes, Chromanones, and Chromones, Volume 31
Substitution of one or two alkyl groups on the C-2 carbon causes slight shifts in the 3- and 4-protons. 85 ~ p m . 5 ~ p mWith . 4= 11 H z ) . 68 ppm. 0 H z . 5-10 H z . ’ Here both the c - 2 and c - 3 protons are shifted upfield. 37,38In most cases a substituent in the 7-position shifts the 3- and 4-protons downfield less than the corresponding substituent in the 5position. The exception to this is 5- and 7-acetyloxy-2H-l-benzopyran, where the C-4 proton is very slightly upfield in the 7- as compared to the 5-isomer.
Eupatoriochromene 6 9 Ac Eupatoriochromene is found in a variety of Australian weeds: Helianthella unifrora Torr. and Grey, Eupatorium riparium Regel, and Encelia calfornica Nutt. Eupatoriochromene is one of six 2H-1-benzopyrans isolated from the extract of these weeds. Its structure was determined on the basis of NMR and the chemical shifts of the C-3 and C-4 protons. 68 ppm (7-OH). G. Evodione ( 3 7 ) 2 4 3 5 9 9 7 0 7 7 1 Evodione is isolated from the volatile oils of a Queensland plant which was mentioned before, Evodia elleryana F.
6' Ageratochromene is the first 2H- I-benzopyran to be isolated from plants belonging to this family. The plants that contain this product are Ageratum mexicanum S i m ~ . 64 Spectral data indicated the following: (a) an ultraviolet spectrum of A,,, (emax) 280 (5500) and 323 nm (9200) showed one carbon-arbon double bondf' (b) infrared absorption showed no hydroxyl or carbonyl groups, but did show gem-dimethyl groups as split methyl peaks at 1383 and 1363 cm-', methyl ether groups, and either a 1,2,3,5- or 1,2,4,5-substituted benzene.