139710-95-5Relevant academic research and scientific papers
Photochromic performance of 1-thiazolyl-2-vinylcyclopentene derivatives having a phenyl-or 4-methoxyphenyl-substituted olefin
Takami, Shizuka,Shimizu, Ayano,Shimizu, Kazuyuki,Miyoshi, Ryota,Yamaguchi, Tadatsugu,Irie, Masahiro
, p. 1059 - 1064 (2013/10/08)
1-Thiazolyl-2-vinylcyclopentene derivatives, 1-(5-methoxy-2-phenyl-4- thiazolyl)-2-(2-methyl-1-phenyl-1-propenyl) perfluorocyclopentene (1a), 1-[5-methoxy-2-(4-methoxyphenyl)-4-thiazolyl]-2-(2-methyl-1-phenyl-1-propenyl) perfluorocyclopentene (2a), and 1-[5-methoxy-2-(4-methoxyphenyl)-4-thiazolyl]-2- [1-(4-methoxyphenyl)-2-methyl-1-propenyl] perfluorocyclopentene (3a) were synthesized in an attempt to obtain yellow photochromic compounds having low photocycloreversion quantum yields and large absorption coefficients of the closed-ring isomers. Their photochromic performance, thermal stability, and fatigue resistance were compared with 1-[5-methoxy-2-(4-methoxyphenyl)-4- thiazolyl]-2-(1,2-dimethyl-1-propenyl)perfluorocyclopentene (4a) having a methyl-substituted olefin. Upon irradiation with 313 nm light, compounds 1a, 2a, and 3a changed from colorless to various shades of yellow in toluene. The conversions from the open-ring (1a, 2a, and 3a) to the closed-ring (1b, 2b, and 3b) isomers in the photostationary state under irradiation with 313nm light were 93, 95, and 98%, respectively. Among the three derivatives 3b has the largest absorption coefficient (= 18900M-1cm-1) at 428nm and the lowest cycloreversion quantum yield of 1.8 10-3.
Neighbouring group participation in the solvolysis of a class of heterocyclic and acyclic trans-dibromides and bromohydrins
Mandal, Asok N,Chatterjee, Amareshwar
, p. 156 - 162 (2007/10/02)
Solvolysis of heterocyclic trans-dibromides and bromohydrins 1a-e affords the ring contracted aldehydes 10a-c and the benzthiophen derivative 11.The acyclic dibromide 2a similarly provides the expected aldehyde 13.Probable pathways for the formation of the products have been presented.
