114183-89-0Relevant academic research and scientific papers
Stereoselectivity in the rhodium(II) acetate catalysed cyclopropanations of 2-diazo-1-indanone with styrenes
Bauta, William,Dodd, John,Bullington, James,Gauthier, Diane,Leo, Gregory,McDonnell, Patricia
, p. 1491 - 1494 (2000)
The rhodium(II) acetate catalysed cyclopropanation reactions of 2- diazo-1-indanone 4 with various substituted styrenes 5 have been investigated. The cyclopropane diastereomer 6a bearing a trans relationship between the carbonyl and the aryl ring was in all cases the predominant isomer and the ratio of stereoisomers almost constant over a range of styrene substituents. Styrenes bearing electron-donating substituents gave slightly better stereoselectivity in favour of the trans isomer. These results are substantiated by a mechanistic proposal. (C) 2000 Published by Elsevier Science Ltd.
Thermal decomposition of some new spiro-1-pyrazolines
Toth,Levai,Dinya,Snatzke
, p. 8119 - 8132 (2007/10/02)
The thermal decomposition of spiro-1-pyrazolines 2 obtained by the cycloaddition of exocyclic α,β-unsaturated ketones with diazomethane gives spirocyclopropanes 4 with high selectivity and the new β-methyl-3-benzylidene derivatives 3. The configuration and conformation of the thermolysis products 3 and 4 were elucidated by different n.m.r. methods.
Rhodium(II) Acetate Catalysed Reactions of 2-Diazo-1,3-indandione and 2-Diazo-1-indanone with Various Substrates
Rosenfeld, M. J.,Shankar, B. K. Ravi,Shechter, H.
, p. 2699 - 2705 (2007/10/02)
Decomposition of 2-diazo-1,3-indandione (3) by rhodium(II) acetate (1) in cyclohexane and in benzene results in overall carbon-hydrogen insertion to give 2-substituted 1,3-indandiones.Anisole, 1, and 3 yield 2-(4-methoxyphenyl)-1,3-indandione (74 percent); benzenes substituted by a single methyl or halogen groups yield the corresponding ortho- and para-substitution products.Spirocyclopropanes are obtained by rhodium(II)-catalyzed additions of 3 to olefins; electron-deficient olefins do not give adducts.Substituted 4H-indenofuran-4-ones and 2,3-disubstituted spiroindene>-1',3'-diones are formed from rhodium(II)-catalyzed reactions of 3 with acetylenes.Reactions of 1 and 3 with cyclohexane, olefins, acetylenes, and arenes involve selective electrophilic carbenic or ylidic processes. 2-Diazo-1-indanone (4) is converted by 1 to 2,2'-bis (48).Thiophenol reacts with 4 and 1 to yield 2-(phenylthio)-1-indanone (49).Cyclopropanations of cyclohexene and styrene by 4 as catalyzed by 1 result in spiroheptane-7,2'-indan>-1-one (50) and 2-phenylspiroinden>-1'(3'H)-one (51), respectively.
