13305-02-7Relevant articles and documents
Novel finding of the effect of triple bond on the photochemical cis-trans isomerization of C=C double bond
Sakakibara, Hirokazu,Ikegami, Masashi,Isagawa, Kakuzo,Tojo, Sachiko,Majima, Tetsuro,Arai, Tatsuo
, p. 1050 - 1051 (2001)
Both cis- and trans-1,2-bis(phenylethynyl)ethenes (1) gave fluorescence emission with considerably high quantum yield and intersystem crossing to the triplet state which underwent cis-trans isomerization. On the basis of the results, a novel potential energy surface of isomerization of 1 was proposed.
STEREOSPECIFIC SYNTHESES OF CIS- AND TRANS-1,6-BISTRIMETHYLSILYL-HEX-3-ENE-1,5-DIYNE
Vollhardt, K. Peter C.,Winn, Libbie S.
, p. 709 - 712 (1985)
Stereospecific syntheses of the title compounds were achieved via the palladium-catalyzed bisethynylation of the vicinal dichloroethenes.
A p-benzyne to m-benzyne conversion through a 1,2-shift of a phenyl group. Completion of the benzyne cascade
Polishchuk, Alexei L.,Bartlett, Kevin L.,Friedman, Lee A.,Jones Jr., Maitland
, p. 798 - 806 (2007/10/03)
Pyrolysis of 1,6-diphenylhexa-1,5-diyne-cis-3-ene at 800-1000 °C leads to a mixture of 1- and 2-phenylbiphenylene, along with triphenylene. Formation of the two biphenylenes is taken as strong evidence of the rearrangement of a p-benzyne into a m-benzyne through a shift of one of the phenyl groups. Copyright
A direct and stereocontrolled route to conjugated enediynes
Jones, Graham B.,Wright, Justin M.,Plourde, Gary W.,Hynd, George,Huber, Robert S.,Mathews, Jude E.
, p. 1937 - 1944 (2007/10/03)
A unified synthetic route to 3-hex-en-1,5-diynes, a key building block found in many of the enediyne antitumor agents and designed materials, was developed. The method, which relies on a carbenoid coupling-elimination strategy is tolerant of a wide range of functionalities, and was applied to the synthesis of a variety of linear and cyclic enediynes. Reaction parameters can be adjusted to control stereoselectivity of the process, producing linear enediynes from 1:12 to >100:1 E:Z ratio, and in the case of cyclic enediynes, giving the exclusively Z C-9, C-10, or C-11 products. Key features of the process are the ready availability of precursors and the mildness and efficiency of the reaction. Application of the process in the design of materials precursors and preparation of enediyne antitumor agents are presented.