84847-61-0Relevant academic research and scientific papers
Ozonolysis of 1-Substituted 2,3-Diphenylindenes and o-(1-Substituted-2-phenyl-3-methoxy-2-propenyl)benzophenones. Remarkable Effects of the Method of Generation of the Carbonyl Oxide Intermediates on the Stereochemistries of Both the Ozonide and the Metha
Nakamura, Norinaga,Fujisaka, Tomohiro,Nojima, Masatomo,Kusabayashi, Shigekazu,McCullough, Kevin J.
, p. 1799 - 1803 (2007/10/02)
Ozonolyses of 1-substituted 2,3-diphenylindenes 1a,b and o-(1-substituted-2-phenyl-3-methoxy-2-propenyl)benzophenones 8a,b in methanol-methylene chloride at -70 deg C, which should proceed through common carbonyl oxide intermediates 11a,b, afforded stereo
Ozonolysis of Vinyl Ethers. Evidence for Intramolecular Oxygen Transfer from a Carbonyl Oxide Moiety to a Methoxyvinyl Group
Nakamura, Norinaga,Nojima, Masatomo,Kusabayashi, Shigekazu
, p. 4969 - 4973 (2007/10/02)
Ozonolysis of diene 1 in carbon tetrachloride gave exclusively the keto ester 2, while in methanol the keto olefin 17 was the major product.The behavior of model vinyl ethers 3a,b has revealed that a mechanism involving intramolecular oxygen atom transfer from the carbonyl oxide moiety to a methoxyvinyl group is the most probable for the keto ester formation from diene 1.
Ozonolysis of 1-Methylindenes. Solvent, Temperature, and Substituent Electronic Effects on the Ozonide Exo/Endo Ratio
Miura, Masahiro,Fujisaka, Tomohiro,Nojima, Masatomo,Kusabayashi, Shigekazu,McCullough, Kevin J.
, p. 1504 - 1509 (2007/10/02)
The ozonolyses of 1-methyl-3-aryl-, 1,2-dimethyl-3-aryl-, and 1-methyl-2,3-diarylindenes (1a-e, 4a-e, 7a-e, 7a',b',d') in various solvents at several temperatures have been undertaken.The data revealed the following. (a) The ozonolysis of indenes 1c, 4c,
Ozonolysis of a Series of 1-Substituted Indenes. The Substituent Steric Effects on Ozonide Exo/Endo Ratios
Miura, Masahiro,Nojima, Masatomo,Kusabayashi, Shigekazu,McCullough, Kevin J.
, p. 2932 - 2936 (2007/10/02)
The ozonolysis of a series of disubstituted (1,2 and 1,3) and trisubstituted (1,2,3) indenes 1-28 in carbon tetrachloride at 20 deg C has been investigated.The major product in each case was the corresponding bicyclic ozonide, usually obtained as a mixtur
Unprecedented Solvolytic Diversion of Carbonyl Oxide Intermediates derived from the Ozonolysis of 1-Methyl-2,3-diphenylindene. Isolation and Characterisation of a Novel Solvent-participated Product
McCullough, Kevin J.,Nojima, Masatomo,Miura, Mashiro,Fujisaka, Tomohiro,Kusabayashi, Shigekazu
, p. 35 - 37 (2007/10/02)
Ozonolysis of 1-methyl-2,3-diphenylindene (1) in methylene chloride-methanol at -70 deg C affords a novel alkoxyhydroperoxide product (3), incorporating methanol, whose crystal structure has been established by X-ray analysis.
Synthesis, X-ray Analysis, and Acidolysis of exo- and endo-1-Methylindene Ozonides
Miura, Masahiro,Ikegami, Akio,Nojima, Masatomo,Kusabayashi, Shigekazu,McCullough, Kevin J.,Nagase, Shigeru
, p. 2414 - 2426 (2007/10/02)
Ozonolyses of 2,3-disubstituted 1-methylindenes gave mixtures of the corresponding exo and endo ozonides.The structures of endo-1-methyl-3-phenylindene ozonide (3a) and exo-1-methyl-2,3-diphenylindene ozonide (2b) were determined by the X-ray analysis.Acidolysis of exo- and endo-1-methylindene ozonides 2a-d and 3a-d under several conditions revealed some characteristic features. (a) Antimony pentachloride or chlorosulfonic acid catalyzed the interconversion of the exo-endo ozonide isomers, the ratio in equilibrium being ca. 7:3 for all the pairs. (b) In the reaction of 3-methyl-substituted indene ozonides 2c,d and 3c,d in acetic-d3 acid-d a rapid hydrogen-deuterium exchange on the bridgehead methyl was observed. (c) In methylene chloride or acetic acid the ozonides decomposed very slowly, yielding the mixtures of rearranged products 4 and 5, carboxylic acid 6, and diketone 7; both the rate of decomposition and the product distribution being a marked function of the structure of the ozonides. (d) Methanol accelerated the decomposition of ozonides, the disappearance following pseudo-first-order kinetics.The rate decreased in the order 3a > 2a > 2b > 2c ca. 3c > 3b.This order was significantly different from the order observed in the reaction in acetic acid: 3b > 3c > 2b > 2c > 3a > 2a. (e) Reduction by AlHCl2 gave a mixture of 3,4-dihydro-1H-2-benzopyrans 19 - 22, the composition being significantly varied depending on the stereochemistry of the ozonides. (f) Treatment of 2a or 3a with bis(α-hydroxy-4-methylbenzyl)peroxide (31) gave two stereoisomeric peroxides 32a and 33a in roughly equal amounts.In contrast, the reaction of an exo ozonide 2d with a mixture of p-tolualdehyde and 30percent H2O2 (an equivalent of 31) afforded exclusively the corresponding exo peroxide 32d, while the endo isomer 3d gave predominantly the endo peroxide 33d.
