13505-34-5Relevant articles and documents
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Micheli,R.A. et al.
, p. 675 - 681 (1975)
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Exceptionally Stable Ozonides. Influence of Methyl Substituents on the Course of Cyclopentene Ozonolyses and on the Reactivities of Ozonides
Mayr, Herbert,Baran, Janusz,Will, Elfriede,Yamakoshi, Hideyuki,Teshima, Koichi,Nojima, Masatomo
, p. 5055 - 5058 (1994)
Ozonolyses of 1,2,3,3,4,4,5,5-octamethyl- (1a), 1,2,3,3,4,4,5-heptamethyl- (1b), and 1,2,3,3,4,4-Hexamethyl cyclopentenes (1c) in methanol did not yield the ordinary hemiperacetals but gave the corresponding ozonides 6a-c instead.The ozonides 6a,b were extremely stable and remained intact even when refluxed with triphenylphosphine in tetrahydrofuran.Cycloreversion of the primary ozonides from unsymmetrically substituted 1,2,3,3-tetramethylcyclopentene (1d) and 1,5,5-trimethylcyclopentene (1f) was highly regioselective to yield intermediate ω-oxo carbonyl oxides with the geminal methyl groups remote from the carbonyl oxide groups.
Stereoselective synthesis of rac-(8R,13S,14S)-7-oxa-estra-4,9-diene-3,17-dione
Kang, Fu-An,Jain, Nareshkumar,Sui, Zhihua
, p. 9021 - 9024 (2006)
The first synthesis of a novel oxa-steroid, rac-(8R,13S,14S)-7-oxa-estra-4,9-diene-3,17-dione has been achieved via stereoselective catalytic hydrogenation of the tetra-substituted indene intermediate, whose structure was confirmed by X-ray crystallography. In contrast to the previous reports of similar indene systems, it was found that catalytic hydrogenation of indenes with a large substituent at the C-2 position and a bulky β-oriented protective group at the C-6 position resulted in cis-indanes instead of trans-indanes.
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Huyser,E.S.,Rose,L.G.
, p. 851 - 853 (1972)
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Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone
Ma, Xiaofeng,Dewez, Damien F.,Du, Le,Luo, Xiya,Markó, István E.,Lam, Kevin
, (2018)
Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.
Dynamic Kinetic Sensitization of β-Dicarbonyl Compounds—Access to Medium-Sized Rings by De Mayo-Type Ring Expansion
Glorius, Frank,Guldi, Dirk M.,Henkel, Christian,James, Michael J.,Mai, Lukas A.,Paulisch, Tiffany O.,Strieth-Kalthoff, Felix
supporting information, (2021/12/27)
Herein, we present a photocatalyzed two-carbon ring expansion of β-dicarbonyl compounds with unactivated olefins that provides facile access to medium-sized rings. Selective sensitization of the substoichiometric enol tautomer enables reactivity of substr
Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone
Ma, Xiaofeng,Du, Le,Luo, Xiya,Markó, István E.,Dewez, Damien F.,Lam, Kevin
, p. 12044 - 12055 (2019/03/01)
Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.
