17397-31-8Relevant academic research and scientific papers
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.
Ring Opening Metathesis Polymerization of Bicyclic α,β-Unsaturated Anhydrides for Ready-to-be-grafted Polymers Having Tailored pH-Responsive Degradability
Kim, Heejin,Kim, Sungwhan,Kang, Sunyoung,Song, Youngjun,Shin, Suyong,Lee, Seonju,Kang, Minji,Nam, So Hee,Lee, Yan
supporting information, p. 12468 - 12472 (2018/09/06)
Polymers having α,β-unsaturated anhydrides as repeating units were synthesized by ring opening metathesis polymerization (ROMP). The anhydride moieties were ready-to-be-grafted with amines to form acid-labile cis-α,β-unsaturated acid amide linkages. The pH-responsive reversible de-grafting can be controlled by changing the intramolecular accessibility between acid and amide groups. The alendronate-grafted ROMP polymers showed distinct pH-dependent cytotoxicity according to the anhydride structures.
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.
Transition metal-catalyzed [4 + 2 + 2] cycloadditions of bicyclo[2.2.1]hepta-2,5-dienes (Norbornadienes) and bicyclo[2.2.2]octa-2,5-dienes
Chen,Kiattansakul,Ma,Snyder
, p. 6932 - 6942 (2007/10/03)
The transition-metal-catalyzed [4 + 2 + 2] cycloadditions of norbornadienes, bicyclo[2.2.2]octa-2,5-diene, and benzobarrelene with 1,3-butadienes proceed in excellent yields using cobalt-based catalytic systems. Two key distinctions between these [4 + 2 + 2] cycloadditions and the corresponding transition-metal-catalyzed [2 + 2 +2] reactions of norbornadiene are the requirement of a bimetal catalytic system with a bisphosphine ligand for the former and exclusive regioselectivity in the [4 + 2 + 2] reaction of 2-substituted norbornadienes to produce 1-substituted adducts. These distinctions may indicate two distinct mechanisms for the [4 + 2 + 2] and [2 + 2 + 2] reactions.
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
Development of a Solar Energy Storage Process. Photoisomerization of a Norbornadiene Derivative to a Quadricyclane Derivative in an Aqueous Alkaline Solution
Maruyama, Kazuhiro,Tamiaki, Hitoshi,Kawabata, Shigeki
, p. 4742 - 4749 (2007/10/02)
In an aqueous alkaline solution, the photoisomerization of norbornadiene derivatives 1 to quadricyclane derivatives 2 was investigated.Upon irradiation with sunlight, 1a-g isomerized quantitatively to 2a-g even in the presence of air, although the reactio
