89942-97-2Relevant academic research and scientific papers
An Efficient Method for the Copper(II)-promoted Stereoselective Iodofunctionalization of Alkenes
Barluenga, Jose,Rodriguez, Miguel A.,Campos, Pedro J.
, p. 2807 - 2809 (2007/10/02)
A mixture of iodine and CuO*HBF4 reacts stereoselectively with alkenes in the presence of a wide variety of nucleophiles (water, MeOH, HCO2H, AcOH, EtCOOH, NaNO2, KSCN, NaSO2Ar, LiCl, LiBr, NaI, Et3SiH, and MeOPh) to give the corresponding 2-functionalized iodo compounds.A regio chemistry study is also reported.
Nitrosonium Ion Promoted Iodination and 1,2-Iodofunctionalization of Cyclohexene
Radner, Finn
, p. 902 - 907 (2007/10/02)
The promoting influence of NO+BF4- on the addition of I2 or 'I+Nu-' couples to cyclohexene (1) in the presence of O2 is described. 1-Acetoxy-2-iodocyclohexane is obtained in 89percent isolated yield from the reaction of I2, 1 and CH3COOH in CH2Cl2, and the corresponding methoxy- and acetamido-substituted iodocyclohexanes are obtained in 96 and 92percent yield, when methanol and acetonitrile, respectively, are added.Applications of the method to the synthesis of cis-1,2-cyclohexanediol (Woodward reaction) and bis(2-iodocyclohexyl) ether is described.
ADDITION OF IODINE-BASED ELECTROPHILIC REAGENTS TO SOME VINYLSILANES
Grayson, Elizabeth J.,Witham, Gordon H.
, p. 4087 - 4094 (2007/10/02)
The addition of some iodine-based electrophilic reagents to the cyclic vinylsilanes (1) and (4, R=But, R1=H) and (4, R=H, R1=OMe) occurs with high regio- and stereo-specificity to give (2, X=OMe, N3 and NCS) and (5, R=But, R1=H, X=OMe and N3) and (5, R=H, R1=OMe, X=OMe).Similar additions to 2-trimethylsilylhept-1-ene (6) are less efficient and occur with lower regioselectivity.Some of the adducts (2) and (5) have been transformed into functionalised organosilanes.Compounds (10, X=OMe, N3, and NCS) and (12)-(15) are thereby obtained.
Supported Reagents in Facile and Selective Two-phase Additions to C=C Double Bonds
Ando, Takashi,Clark, James H.,Cork, David G.,Fujita, Mitsue,Kimura, Takahide
, p. 1301 - 1302 (2007/10/02)
Inorganic-solid-supported KSCN, NaN3, and KOAc mixed with iodine and an alkene in CHCl3 gave products by a facile two-phase addition.
The Synthesis and Some Reactions of Thiazolidine-2-selones
Cambie, Richard C.,Rutledge, Peter S.,Tan, Vivien Y. Y.,Woodgate, Paul D.
, p. 3655 - 3694 (2007/10/02)
As a route to thiazolidine-2-selones or the tautomeric 2-thiazolines, the reactions of trans-1-iodo-2-isothiocyanatocyclohexane with selenium nucleophiles have been investigated.Sodium hydrogenselenide gives a mixture of the 2-selone (2) and 2-thione (3) while lithium selenide gives mainly the 2-thione (3).With these reagents trans-1-iodo-2-isocyanatocyclohexane gives the corresponding selenazolidin-2-one (5).Treatment of 2-lithiobenzothiazole with N-phenylselenophthalimide or diphenyl diselenide gives 2-phenylselenobenzothiazole, while reaction of the sodium salt of selenobenzothiazole with alkyl or allyl halides affords high yields of 2-alkylseleno- and 2-allylselenobenzothiazoles, respectively.Treatment of 2-decylselenobenzothiazole with either hydrogen peroxide or m-chloroperbenzoic acid leads to low yields of the Pummerer rearrangement product (40). 2-Prop-2'-enylselenobenzothiazole can be used as a transfer reagent in palladium-catalysed allylation of diethyl malonate.Alternative routes to vic-iodoselenocyanates have been investigated.
vic-Iodothiocyanates and Iodoisothiocyanates. Part 8. Addition of Iodine-Thiocyanogen to Alkenes under Ionic and Radical Conditions
Cambie, Richard C.,Rutledge, Peter S.,Strange, Gary A.,Woodgate, Paul D.
, p. 553 - 565 (2007/10/02)
Addition of iodine-thiocyanogen to alkenes in the dark proceeds by a regioselective ionic reaction to give mainly vic-iodoisothiocyanates, and under irradiation with u.v. light by a radical reaction to give mainly vic-iodothiocyanates.However, in the case of 1-methylene-4-t-butylcyclohexane even under irradiation by u.v. light, ionic addition of the reagent competes successfully with, and almost to the exclusion of, the radical pathway.
REACTION OF OLEFINS WITH A MIXTURE OF IODINE AND MERCURY(II) THIOCYANATE. PREDOMINANT FORMATION OF vic-IODO(ISOTHIOCYANATO)ALKANES.
Watanabe,Uemura,Okano
, p. 2458 - 2462 (2007/10/02)
Treatment of olefins with a mixture of iodine and mercury(II) thiocyanate in benzene or diethyl ether gives vic-iodo(isothiocyanato)alkanes and vic-iodo(thiocyanato)alkanes in a high yield, the former being predominant. Similar results were obtained by us
vic-Iodothiocyanates and Iodoisothiocyanates. Part 3. Further Preperations, and the Formation of 2-Alkoxy-2-thiazolines
Cambie, Richard C.,Chambers, David,Rutledge, Peter S.,Woodgate, Paul D.,Woodgate, Shella D.
, p. 33 - 39 (2007/10/02)
The reactions of (E)-hex-3-ene, 4-t-butylcyclohexene, and 3-t-butylcyclohexene with iodine and potassium thiocyanate are examined.The action of iodine and thiocyanogen with (E)-hex-3-ene gives different results from those reported in the literature.Isomerization of the vic-iodothiocyatates and formation of 2-alkoxy-2-thiazolines from the latter adducts are reported.
