23904-33-8Relevant academic research and scientific papers
A STEREOSELECTIVE SYNTHESIS OF (Z)-1-IODO-1-ALKENES
Stork, Gilbert,Zhao, Kang
, p. 2173 - 2174 (1989)
(Z)-1-iodo-1-alkenes can be synthesized stereoselectively via the Wittig reaction of iodomethylenetriphenylphosphorane with aldehydes.
Stereospecific Iron-Catalyzed Carbon(sp2)-Carbon(sp3) Cross-Coupling with Alkyllithium and Alkenyl Iodides
Lu, Xiao-Lin,Shannon, Mark,Peng, Xiao-Shui,Wong, Henry N. C.
supporting information, p. 2546 - 2549 (2019/03/26)
An efficient synthetic protocol involving iron-catalyzed cross-coupling reactions between organolithium compounds and alkenyl iodides as key coupling partners was achieved. More than 30 examples were obtained with moderate to good yields and high stereospecificity. Gram-scale and synthetic applications of this procedure are recorded herein to demonstrate its feasibility and potential utilization.
A New Entry of Practical and Chemoselective Iodocarbenoids for Carbonyl Iodomethylenation
Yan, Tu-Hsin,Chen, Mei-Yuan
, p. 390 - 394 (2017/04/24)
Direct oxidative addition of CHI3 to the Mg-TiCl4 bimetallic species resulted in the generation of a highly chemoselective and practically convenient iodomethylenetitanium complex, which efficiently effected condensation even with enolizable or inert carbonyl compounds, such as sterically congested ketones, to provide vinyl iodide compounds.
Synthesis of alkenyl sulfides through the iron-catalyzed cross-coupling reaction of vinyl halides with thiols
Lin, Yun-Yung,Wang, Yu-Jen,Lin, Che-Hung,Cheng, Jun-Hao,Lee, Chin-Fa
experimental part, p. 6100 - 6106 (2012/10/08)
We report here the iron-catalyzed cross-coupling reaction of alkyl vinyl halides with thiols. While many works are devoted to the coupling of thiols with alkyl vinyl iodides, interestingly, the known S-vinylation of vinyl bromides and chlorides is limited
Halodephosphorylation of α,β-unsaturated phosphonic acid monoesters
Lahrache, Hind,Robin, Sylvie,Rousseau, Gérard
, p. 1635 - 1637 (2007/10/03)
Reaction of α,β-ethylenic and acetylenic phosphonic acid monoesters with (biscollidine)iodine(I) or (biscollidine)bromine(I) hexafluorophosphate led to α,β-unsaturated halides by, without precedent, dephosphorylation reactions.
The regiochemistry and stereochemistry of α,β-epoxysilane ring opening with silyl halides or pseudohalides
Bassindale, Alan R.,Soobramanien, Marie-Claire,Taylor, Peter G.
, p. 604 - 608 (2007/10/02)
The reaction of trimethylsilyl halides with α,β-epoxysilanes leads to either a vinyl halide by addition/elimination or a vinyl enol ether by rearrangement; the route depends upon the nature of the groups attached to the epoxyde ring.With groups β to the silicon that can stabilise an adjacent positive charge the directive effect of silicon towards substitution at the α position is overcome such that the enol ether is obtained.Trimethylsilyl pseudohalides behave similarly except that the intermediate addition product can be isolated.The stereoselectivity of ring opening is found to vary with the reagent. epoxyde / epoxysilane / ring opening / regiochemistry / halosilane
A new Procedure for the Synthesis of (E)-1-iodo-1-alkenes
Martinez, A. Garcia,Alvarez, R. Martinez,Gonzalez, S. Martinez,Subramanian, L. R.,Conrad, M.
, p. 2043 - 2044 (2007/10/02)
(E)-1-iodo-1-alkenes 4 can be prepared stereoselectively from aldehydes 1 via IH-elimination of 1,1-di-iodoalkanes 3 with DBU. Key words: Vinyl iodide; diiodoalkane; elimination; stereoselectivity.
Photochemistry of Alkyl Halides. 9. Geminal Dihalides
Kropp, Paul J.,Pienta, Norbert J.
, p. 2084 - 2090 (2007/10/02)
The photobehavior of the geminal dihalides (diiodomethyl)cyclohexane (7), (bromoiodomethyl)cyclohexane (11), (dibromomethyl)cyclohexane (17), (diiodomethyl)cyclopentane (22), 3,3-dimethyl(diiodomethyl)cyclobutane (27), and 8,8-diiodo-2,6-dimethyl-2-octene (31) has been studied and compared with that previously observed for diiodomethane.In all solvents the corresponding vinyl halides (iodomethylene)cyclohexane (13), (bromomethylene)cyclohexane (21), (iodomethylene)cyclopentane (23), 3,3-dimethyl(iodomethylene)cyclobutane (28), or cis- and trans-3,7-dimethyl-1-iodo-1,6-octadiene (33) were obtained, which are thought to arise from α-halo cationic intermediate formed via initial light-induced homolytic cleavage of the carbon-iodine bond followed by electron transfer within the resulting caged radical pair, as shown in Schemes II and III.In the case of diiodide 31 competing intramolecular trapping of the α-iodo cation afforded in addition the cyclized isopulegyl iodide (34).In polar solvents the vinyl iodides were accompanied by the nonhalogenated products methylenecyclohexane (15), 1-methylcyclopentene (25), cyclohexene (26), 4,4-dimethylcyclopentene (29), and cis- and trans-carane (35), which are thought also to arise from the α-halo cationic intermediate. 1.1-Diiodo-2,2-dimethylpropane (1b) afforded 2-methyl-2-butene (6b).Except for carane (35) from diiodide 31 there was no detectable formation of cyclopropanes.In methanol the nucleophilic substitution products (dimethoxymethyl)cyclohexane (14), (dimethoxymethyl)cyclopentane (24), and 1,1-dimethoxy-2,2-dimethylpropane (30) were obtained.It is concluded that geminal dihalides undergo predominant, if not exclusive, photoreaction via initial clea vage of a single carbon-halogen bond in analogy with monohalides and that carbene intermediates are not formed.A similiar conclusion has been reached previously for diiodomethane in the photocyclopropanation of alkenes.
Photochemistry of Alkyl Halides. 10. Vinyl Halides and Vinylidene Dihalides
Kropp, Paul J.,McNeely, Steven A.,Davis, Robert Drummond
, p. 6907 - 6915 (2007/10/02)
The photobehavior of the acyclic vinyl iodide 2, the 1-iodocycloalkenes 11-14 and 39, the (halomethylene)cycloalkanes 45-48, and the (dihalomethylene)cyclohexanes 62-64 has been studied.Except for the dichloride 64, which exhibited only radical behavior, each of the halides afforded a mixture of ionic and radical products.The two bromides studied, 48 and 63, afforded lower ratios of ionic to radical products than the corresponding iodides 45 and 62.Irradiation of vinyl iodides was found to be a convenient and powerful method for the generation of vinyl cations, including the highly strained 1-cyclohexenyl and 1-cyclopentenyl cations and the unstabilized α-unsubstituted cations 51 and 54.The latter cations underwent rearrangement to the ring-expanded 1-cycloalkenyl cations 28 and 36, respectively.Lowering the temperature of the irradiation of iodides 13, 14, and 45 resulted in an increased ratio of ionic to radical products.However, iodide 47, which underwent principally fragmentation to enyne 61, showed little temperature effect.
