17397-31-8Relevant articles and documents
Structure and NMR spectra of bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid and its Anhydride
Aitken, R. Alan,Fotherby, Fiona M.,Slawin, Alexandra M.Z.
, (2021/10/07)
Two of the three published sets of 1H and 13C NMR data for bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic anhydride have been found to actually be those of the corresponding diacid. The NMR spectroscopic distinction between these two compounds is clarified and 1JC–H values are reported for the anhydride, the diacid and a related diester. The X-ray structure of the diacid has been determined and features chains of molecules involving both intra- and inter-molecular hydrogen bonding.
The preparation of 7-substituted norbornadiene-2,3-dicarboxylic anhydrides and an experimental and theoretical study of their reactivity
Margeti?, Davor,Warrener, Ronald N.,Sun, Guangxing,Butler, Douglas N.
, p. 4338 - 4346 (2007/10/03)
Four new substituted methano-bridged or heteroatom-bridged norbornadienomaleic anhydrides have been prepared and converted to sesquinorbornadiene anhydrides by reaction with cyclic 1,3-dienes. The versatility of parity reversal, in conjunction with N-substituent steric effects, has been used to produce all three possible stereoisomers of the N,O-sesquinorbornadiene anhydrides in separate, stereoselective cycloadditions. The anhydrides have been synthesized by cyclization of their diacids (in situ production) or by flash vacuum pyrolysis of their furan adducts (yielding crystalline products); further fragmentation occurs at these or higher temperatures to produce five-membered carbocyclic or heterocyclic anhydrides. Activation energies have been evaluated for the fragmentation and cycloaddition processes using DFT calculations (B3LYP/6-31G*) and these calculations correctly predict, which reaction can be intercepted at the norbornadienomaleic anhydride stage and preferred stereochemistry of cycloadducts.
The Pyrolysis of Butatrienone Precursors: 3,4-Diazatricyclo2,6>deca-3,8-diene-endo-cis-2,6-dicarboxylic Anhydride and its 5,5-Diphenyl Derivative
Anderson, Mark R.,Brown, Roger F. C.,Browne, Neil R.,Eastwood, Frank W.,Fallon, Gary D.,et al.
, p. 549 - 560 (2007/10/02)
Flash vacuum pyrolysis of the title anhydride (4) gave a poor yield of butatrienone, detected by argon matrix isolation infrared spectroscopy.Similar pyrolysis of the 5,5-diphenyl derivative (8) failed to give diphenylbutatrienone: the red product (16) is
