A comprehensive study of the solvent effects on the cycloaddition reaction of diethyl azodicarboxylate and ethyl vinyl ether: Efficient implementation of QM and TD-DFT study

2014 ◽  
Vol 115 (6) ◽  
pp. 381-388 ◽  
Author(s):  
Mohammad Khavani ◽  
Mohammad Izadyar
Keyword(s):  
Vinyl Ether ◽  
Solvent Effects ◽  
Cycloaddition Reaction ◽  
Efficient Implementation ◽  
Dft Study ◽  
Ethyl Vinyl Ether ◽  
Ethyl Vinyl ◽  
Td Dft ◽  
Diethyl Azodicarboxylate ◽  
Comprehensive Study

Article

1999 ◽  
Vol 77 (5-6) ◽  
pp. 868-874
Author(s):  
Maike Fischer ◽  
Yijian Shi ◽  
Bao-ping Zhao ◽  
Victor Snieckus ◽  
Peter Wan
Keyword(s):  
Aqueous Solution ◽  
Vinyl Ether ◽  
Hydroxy Group ◽  
Ground State ◽  
Cycloaddition Reaction ◽  
Quinone Methide ◽  
Quantum Yields ◽  
Ethyl Vinyl Ether ◽  
High Chemical ◽  
Ethyl Vinyl

The photosolvolysis of 1- and 2-hydroxy-9-fluorenols 4-6 has been studied in aqueous solution. All of these 9-fluorenols photosolvolyze efficiently in 1:1 H2O-CH3OH, to give the corresponding methyl ether products in high chemical and quantum yields. Whereas the photosolvolysis of the parent 9-fluorenol (2, R = H) is known to proceed via the very short-lived and formally ground-state antiaromatic 9-fluorenyl cation (1, R = H), the photosolvolysis of 1-hydroxy-9-fluorenol (4) proceeds via a much longer-lived (approximately = 5-10 s) fluorenyl quinone methide 9, which is trappable by ethyl vinyl ether via a [4+2] cycloaddition reaction to give a chroman derivative. Interestingly, 2-hydroxy-9-fluorenol (5) photosolvolyzes via a very short-lived intermediate with similar lifetimes as observed for the 9-fluorenyl cation (1, R = H), although a corresponding fluorenyl quinone methide intermediate is accessible for this compound. This study demonstrates that the mechanism of photosolvolysis of these types of compounds can be dramatically altered when an aryl hydroxy group is present.Key words: photosolvolysis, 9-fluorenyl cation, quinone methide, carbocation, antiaromatic.

Computational Study on the Mechanism of Cycloaddition Reactions of Bissulfonyl-1,3-butadiene with Some Alkenes

2020 ◽  
Vol 17 (10) ◽  
pp. 735-742
Author(s):  
Sepideh Masoumifar ◽  
Mina Haghdadi ◽  
Hassan Ghasemnejad Bosra
Keyword(s):  
Vinyl Ether ◽  
Energy Barrier ◽  
Computational Study ◽  
Cycloaddition Reaction ◽  
Dft Method ◽  
Ethyl Vinyl Ether ◽  
Cycloaddition Reactions ◽  
Ethyl Vinyl

The cycloaddition reactions of 2,3-bis (ethylene sulfonyl)-1,3-butadiene with 2,3-dimethyl- 1,3-butadiene, cyclopentadiene, 2-methyl prop-2-enoate and ethyl vinyl ether have been theoretically studied using the DFT method at the MPWB1K/cc-pVDZ level of theory. There are two possible modes of participation in each reaction (2π and 4π electron), of which the 2π electron is preferred. The energy results indicate that formations of the [2+4] cycloadducts are favored kinetically. The stereoselectivity of the [2+4] cycloaddition reaction of 2,3-bis (ethylene sulfonyl)-1,3-butadiene with cyclopentane is the highest and the energy barrier for this process is the lowest.

Ethyl Vinyl Ether

1955 ◽  
Vol 34 (4) ◽  
pp. 235???240 ◽  
Author(s):  
Max S. Sadove ◽  
Gordon M. Wyant ◽  
John O. Cletcher
Keyword(s):  
Vinyl Ether ◽  
Ethyl Vinyl Ether ◽  
Ethyl Vinyl
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