16554-84-0Relevant academic research and scientific papers
Thermal rearrangements of 7,7-dihalo-trans-bicyclo[4.1.0]hept-3-enes.
Gassman, Paul G.,Han, Sangdon,Chyall, Leonard J.
, p. 5459 - 5462 (1998)
Derivatives of trans-bicyclo[4.1.0]hept-3-ene with chlorine and bromine substituents the 7 position were synthesized and their thermal rearrangements were examined. Thermolysis of the dichloride leads to the formation of the cis-fused isomer, while heating the dibromide results in ring-expanded products. Thermal rearrangement of the bromochloro derivative provided a mixture of ring-isomerized and ring-expanded products. The halogenated compounds are very labile relative to the unsubstituted molecule with rate accelerations on the order of 1000 or more at 120 °C. When solvents of widely varying polarity were employed, the isomerization rate coefficients for the halogenated derivatives vary by a factor of 1.0-3.2. Therefore, it is unlikely that these compounds rearrange via ionic intermediates.
Novel ambiphilic dichlorocarbenoid equivalent in alkene cyclopropanation and carbonyl olefination
Chien, Ching-Ting,Tsai, Chia-Chung,Tsai, Chi-Hui,Chang, Tsai-Yuan,Tsai, Ping-Kuei,Wang, Ying-Chuan,Yan, Tu-Hsin
, p. 4324 - 4327 (2007/10/03)
The Ti-Mg-dichloromethylene complexes derived from the oxidative addition of CCl4 to the Mg-TiCl4 bimetallic species serve as a novel class of ambiphilic dichlorocarbenoid equivalents. Not only is Ti-Mg-dichlorocarbenoid highly selective but also it seems highly reactive in both alkene cyclopropanations and carbonyl dichloromethylenations.
LES (TRIMETHYLSILYL)BICYCLO-ALCENES, NOUVEAUX SILYLCYCLOPROPANES BICYCLIQUES FONCTIONNELS
Grignon-Dubois, M.,Dunogues, J.,Ahra, M.
, p. 216 - 225 (2007/10/02)
A convenient synthesis of new silylbicyclo-alkenes is reported involving a facile and rapid process and giving both endo and exo monosilyl isomers as well as gem-disilyl derivatives.The behaviour of these species towards acids has been investigated.Both the size of the large ring and the double-bond position play a role in the regiochemistry of the electrophilic attack.These results bring to ligth new perspectives for functionalization of cyclololefins via cyclopropanation.
Attempted Synthesis of Some α-Halolactones Fused in Bicycloheptanes
Hashem, Md. Abul
, p. 424 - 429 (2007/10/02)
For the synthesis of the lactones A, B and C, compounds 4a, 4b, 10a and 10b were synthesized by dihalocyclopropanation and epoxidation of the dienes 1 and 7. 4a and 10a on hydrolysis give the corresponding diols 11 and 12.Treatment of 10a and 10b with BuLi/CO2 at -90 deg C gives the α-halocarboxylic acids 13a and 13b respectively.Both 13a and 13b on hydrolysis with 2N H2SO4 in acetone afford polymeric material, from which no pure product could be isolated.A dihydroxy-α-chlorocyclopropyl ester (17) has been synthesized from 1 but no lactone could be isolated.
Synthesis and Reactions of 1,6-Dithiocyanato- and 1,6-Diiodo-1,3,5-cycloheptatrienes
Okazaki, Renji,O-oka, Masaharu,Tokitoh, Norihiro,Inamoto, Naoki
, p. 180 - 185 (2007/10/02)
Photoreactions of benzocyclopropene (1) wiyh thiocyanogen and iodine afforded 1,6-dithiocyanato- (4) and 1,6-diiodocycloheptatriene (7), respectively, in good yields, whereas thermal reactions gave 2-thiocyanatobenzyl thiocyanate (5) and 2-thiocyanatobenz
