119333-55-0Relevant academic research and scientific papers
DIASTEREOTOPIC SELECTION OF C2 HYDROGENS IN THE REARRANGEMENT OF C1-SUBSTITUTED EPOXIDES: AN EXAMINATION OF STYRENE OXIDE
Coxon, J. M.,McDonald, D. Q.
, p. 2575 - 2576 (1988)
Rearrangement of styrene oxide with (a) LiClO4 and (b) BF3 to give phenylethanal exhibits diastereotopic selection with migration of the hydrogen trans to the phenyl group being favoured 1.4 and 1.14 times respectively.The rate of rotation about the C1-C2
Oxygenation of Styrene by Cytochrome P-450 Model Systems: A Mechanistic Study
Collman, James P.,Kodadek, Thomas,Brauman, John I.
, p. 2588 - 2594 (2007/10/02)
The manganese and iron porphyrin catalyzed oxygenation of styrene results in the production of phenylacetaldehyde as well as the expected epoxide.It is demonstrated that aldehyde is a primary product and dose not result from isomerization of styrene oxide.Isotope labeling studies show that one of the β hydrogen atoms of styrene migrates to the benzylic carbon in the course of aldehyde formation.Experiments using cis and trans deuterated styrenes reveal that there is a stereoelectronic preference for migration of the hydrogen cis to the aromatic ring.Styrene, styrene-d8, and cis-β-deuteriostyrene yield similar ratios of epoxide to aldehyde, indicating that β hydrogen migration occurs after the rate-determining step for formation of phenylacetaldehyde.The mechanism of this rearrangement is discussed.Some new information concerning the mechanism of olefin epoxidation by these catalysts is also presented.These results may have relevance to the mechanism of alkene oxygenation by the cytochrome P-450 monooxygenase enzymes.
10-ALKENYLPHENOTHIAZINES. SYNTHESIS AND MECHANISM OF ACIDIC HYDROLYSIS OF cis- AND trans- 10-(2-PHENYLVINYL)PHENOTHIAZINES
Anfinogenov, V. A.,Napilkova, O. A.,Sirotkina, E. E.,Filimonov, V. D.,Khlebnikov, A. I.
, p. 1152 - 1157 (2007/10/02)
The addition of phenothiazine to phenylacetylene in super-base media proceeds regio- and stereoselectively and leads to the predominant formation of cis-10-(2-phenylvinyl)phenothiazine, which is completely converted to its trans-isomer at 200 deg C.Kinetic analysis of the acid hydrolysis of the cis- and trans- isomers has alloved us to assign to it an ACE2 reaction mechanism, similar to the mechanism of hydrolysis of vinyl alkyl ethers.
