Iodo-l-propene

SYNS 3-IODOPROPENE 3-IODO-l-PROPENE 3-lODOPROPYLENE 1-PROPENE, 3-IODO-(9CI)... 

Alternatively, 2-(chloromethyl)-3-iodo-l-propene reacted with aldehydes or ketones to give after basic treatment methylenetetrahydrofuran in excellent yields. The reaction is as expected chemo- and regioselective conjugated carbonyl compounds gave 1,2-addition, and aldehydes react more preferably than ketones [106]. Simharly, 3-chloro-homoallylic alcohols were prepared in high yields from the reaction of 2,3-dichloropropene with carbonyl compounds in a two-phase system containing a small amount of acetic acid. In this reaction, the presence of water in the reaction medium was shown to be essential as the reaction did not occur under non-aqueous conditions [107]. 

Another bifunctional compound, 2-(chloromethyl)-3-iodo-l-propene, was allowed to react in the same conditions with aldehydes or ketones, providing, after basic treatment, methylenetetrahydrofurans in high yield. The allyla-tion is regioselective conjugated carbonyl compounds reacted in a 1,2-fashion. It is also chemoselective, as evidenced by a competitive experiment between 5-nonanone and benzaldehyde (Li and Chan, 1991a) ... 

Chan and Li reported that conjugated 1,3-butadienes were produced in moderate yields when carbonyl compounds reacted with 1,3-dichloropropene and zinc in water (Eq. 8.29).61 The use of 3-iodo-1-chloropropene instead of 1,3-dichloropropene greatly improved the yields. When the reactions were interrupted after their initial allyla-tions, subsequent base treatment of the intermediate compounds produced vinyloxiranes in high yields. Similarly, reactions of carbonyl compounds with 3-iodo-2-chloromethyl-l-propene followed by base treatment produced 2-methylenetetrahydrofurans (Eq. 8.30).62 Thus, the 3-iodo-2-chloromethyl-l-propene served as a novel trimethylene-methane equivalent.63... 

The reaction of phenyl-1,2-propadiene with iodine bromide in MeOH afforded a 100% yield of 2-iodo-3-phenyl-3-methoxy-l-propene whereas the reaction in CS2 at 0°C provided a l 4mixture of 2-iodo-3-phenyl-3-bromo-l-propene and l-phenyl-2-iodo-3-bromo-l-propene [16]. The corresponding chlorination shows a lower regios-... 

C4H7I 1 -iodo-2-rriethyl-l -propene 20687-01-8 173.36 9.414 2 3508 C4H802 ethyl acetate 141-78-6 189.60 10.480 1... 

The mixed halogens ICl, IBr, and BrCl also add to alkenes. White and Robertson found third-order kinetics for the reaction and determined the relative reactivities to be BrCl > ICl > Br2 > IBr > l2- The l ge reactivity of BrCl means that addition of BrCl can occur when alkenes react with mixtures of Br2 and Cl2. The regioselectivity of addition of mixed halogens was reported by Ingold and Smith. Addition of ICl to propene gave 69% of 2-chloro-l-iodo-propane (30) and 31% of l-chloro-2-iodopropane (31), and addition to styrene gave more than 95% of l-chloro-2-iodo-l-phenylethane. ... 

Related Reagents. 3-Acetoxy-2-trimethylsilylmethyl-l-propene 1 3-Iodo-2-trimethylsilylmethyl-l-propene. 

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