Stereochemistry of Disilanylene-Containing Cyclic Compounds. Thermal Reactions of cis- and trans-3,4-Benzo-1,2-diisopropyl-1,2-dimethyl-1,2-disilacyclobut-3-ene

2013 ◽  
Vol 32 (21) ◽  
pp. 6476-6487 ◽  
Author(s):  
Akinobu Naka ◽  
Junnai Ikadai ◽  
Jun Sakata ◽  
Mitsuo Ishikawa ◽  
Yoshihiro Hayashi ◽  
...  
Keyword(s):  
Thermal Reactions ◽  
Cyclic Compounds ◽  
Cis And Trans

Chromatographic study of thermal reactions of cis- and trans-[Coen2 (OCOC6H4X)2]NO3 complexes in the solid phase

1977 ◽  
Vol 19 (1) ◽  
pp. 85-92 ◽  
Author(s):  
V. Carunchio ◽  
G. Grassini Strazza ◽  
A. Messina ◽  
C.M. Polcaro
Keyword(s):  
Solid Phase ◽  
Chromatographic Study ◽  
Thermal Reactions ◽  
Cis And Trans

Diels-Alder Reactions With Unsaturated Sulfoxides. Reactions of (Z)-3-Phenylsulfinylprop-2-Enoic Acid and Methyl-Ester With Furan, 1,3-Diphenylisobenzofuran and Anthracene

1986 ◽  
Vol 39 (4) ◽  
pp. 575 ◽  
Author(s):  
K Picker ◽  
SM Proust ◽  
DD Ridley
Keyword(s):  
Methyl Ester ◽  
High Temperatures ◽  
Low Temperatures ◽  
Diels Alder ◽  
Enoic Acid ◽  
Reaction Conditions ◽  
Thermal Reactions ◽  
Cis And Trans

Methyl (Z)-3-phenylsulfinylprop-2-enoate undergoes Diels -Alder reactions with furan, 1,3-diphenylisobenzofuran and anthracene but chemical and stereochemical courses of the reactions are very dependent upon reaction conditions. Thus, with furan, cis,endo - and cis,exo - adducts are formed exclusively; with 1,3-diphenylisobenzofuran cis,endo - and cis,exo -adducts are formed at low temperatures, whilst the corresponding trans-adducts are formed upon heating; with anthracene where high temperatures are required for condensation cis- and trans-adducts arise together with products from further thermal reactions.

Stereochemistry of Disilanylene-Containing Cyclic Compounds. Palladium-Catalyzed Reactions of cis- and trans-3,4-Benzo-1,2-diisopropyl-1,2-dimethyl-1,2-disilacyclobut-3-ene with Ethylene

2012 ◽  
Vol 31 (9) ◽  
pp. 3492-3498 ◽  
Author(s):  
Akinobu Naka ◽  
Joji Ohshita ◽  
Eigo Miyazaki ◽  
Toshiko Miura ◽  
Hisayoshi Kobayashi ◽  
...  
Keyword(s):  
Palladium Catalyzed ◽  
Catalyzed Reactions ◽  
Cyclic Compounds ◽  
Cis And Trans

Stereochemistry of Disilanylene-containing Cyclic Compounds – Synthesis and Palladium-catalyzed Reactions of cis- and trans-3,4- Benzo-1,2-diisopropyl-1,2-dimethyl-1,2-disilacyclobut-3-ene

2009 ◽  
Vol 64 (11-12) ◽  
pp. 1580-1590 ◽  
Author(s):  
Akinobu Naka ◽  
Jun Sakata ◽  
Junnai Ikadai ◽  
Hiroyuki Kawasaki ◽  
Joji Ohshita ◽  
...  
Keyword(s):  
Catalytic Amount ◽  
Similar Reaction ◽  
Single Isomer ◽  
Palladium Catalyzed ◽  
Catalyzed Reactions ◽  
Cyclic Compounds ◽  
Cis And Trans

The synthesis and palladium-catalyzed reactions of cis- and trans-3,4-benzo-1,2-diisopropyl- 1,2-dimethyl-1,2-disilacyclobut-3-ene (1a and 1b) are reported. Their reactions with diphenylacetylene in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium(0) proceeded with high stereospecificity to give cis- and trans-5,6-benzo-1,4-diisopropyl-1,4-dimethyl- 2,3-diphenyl-1,4-disilacyclohexa-2,5-diene, 2a and 2b, in 95% and 93% yield, respectively. Similar palladium-catalyzed reactions of 1a and 1b with monosubstituted acetylenes, such as 1-hexyne, tert-butylacetylene, phenylacetylene, and trimethylsilylacetylene, also proceeded stereospecifically to afford the respective cis- and trans-5,6-benzo-1,4-disilacyclohexa-2,5-dienes, 3a - 6a and 3b - 6b, in excellent yields and as the sole products. The palladium-catalyzed reaction of 1a with styrene gave a mixture consisting of two stereoisomers, cis-2- and trans-2-phenyl-substituted 5,6- benzo-(r-1),cis-4-diisopropyl-1,4-disilacyclohex-5-ene 7a and 8a in a ratio of 5 : 3 in 72% combined yield, while the reaction of styrene with 1b afforded two stereoisomers, 7b and 8b, in a ratio of 2 : 1 in 80% combined yield. With 1-hexene, 1a gave two stereoisomers, 5,6-benzo-cis-2-(nbutyl)-( r-1),cis-4-diisopropyl- and 5,6-benzo-trans-2-(n-butyl)-(r-1),cis-4-diisopropyl-1,4-dimethyl- 1,4-disilacyclohex-5-ene, 9a and 10a, in a ratio of 1 : 1 in 70% combined yield. A similar reaction of 1b with 1-hexene produced 5,6-benzo-cis-2-(n-butyl)-(r-1),trans-4-diisopropyl-1,4-dimethyl-1,4- disilacyclohex-5-ene in 81% yield and as a single isomer

Article

1999 ◽  
Vol 77 (5-6) ◽  
pp. 647-653
Author(s):  
Robert P Claridge ◽  
Ross W Millar ◽  
John H Ridd
Keyword(s):  
Nitrogen Dioxide ◽  
Nuclear Polarization ◽  
Straight Chain ◽  
Absorption Signal ◽  
Emission Signal ◽  
Enhanced Absorption ◽  
Reverse Mode ◽  
Diallyl Ether ◽  
Cyclic Compounds ◽  
Cis And Trans

The reaction of diallyl ether with nitrogen dioxide in organic solvents yields a mixture of cis and trans 2,3-bis(nitromethyl)tetrahydrofurans, cis and trans 2-nitratomethyl-3-nitromethyltetrahydrofurans and a number of straight-chain compounds with one to four nitro groups. Under the conditions used, the cyclic compounds form the main products when the solution of nitrogen dioxide is slowly added to the solution of diallyl ether but not when the reverse mode of addition is used. When 15N-nitrogen dioxide is used, the products show strong 15N nuclear polarization: the 2,3-di(nitromethyl)tetrahydrofurans give an emission signal, and one straight-chain product with two nonequivalent nitro groups shows both an emission signal and an enhanced absorption signal. For both the cyclic and straight-chain products, the nuclear polarization is consistent with the successive reactions of diallyl ether with two nitrogen dioxide radicals with uncorrelated spins.Key words: diallyl ether, nitrogen dioxide, 15N nuclear polarization, CIDNP.

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