3- Chloro-2-methyl-l-propene

Chloromethylphenyl acetate, (4-Acetoxyphenyl)methyl chloride, see 4-Acetoxybenzyl chloride, 3132b 2-Chloro-5-methylphenylhydroxylamine, 2792 Chloromethylphenylsilane, 2806 f 3-Chloro-2-methyl-l-propene, 1548 2-Chloromethylthiophene, 1836 A-Chloro-3-morpholinone, 1485 /V- C h I o ro -4 - n i t ro a n i I i n e, 2224 2-Chloro-5-nitrobenzaldehyde, 2645 2-Chloro-6-nitrobenzaldehyde, 2646... 

The preparation of dicarbonyl(T -cyclopentadienyl)(2-methyl-l-propenyl-KC )iron requires 3-chloro-2-methyl-l-propene (methailyl chloride), not the reagent given in Reference 1, p. 165. ... 

P-methylallyl chloride. (methallyl chloride 3-chloro-2-methyl-l-propene MAC). CH2 C(CH3)CH2C1. 

Chloro-2-methyl-l-propene A134 Industrial 129P... 

Chloro-2-methyl-l- propene C1-CH2C(CH3)=CH2 66.2 277.0 Correlation 1995DEN... 

A typical reaction involving nickel(O) treats an allylic halide such as 3-chloro-2-methyl-l-propene with Ni(CO)4 to form 439,288 a nickel dimer analogous to the palladium chloride dimer discussed in the previous section. This complex reacts with an alkene to form a new complex (440), and subsequent reaction with a variety of electrophilic reagents removes nickel. In this example, the chlorine was converted to an acetate ligand (in 441) and reacted with methanolic carbon monoxide to give the ester (442).288... 

In iron reactions where the reagent was equivalent to C, described in Section 8.9.A, the iron moiety was used as an auxiliary. Iron can also stabilize cations, which then react with nucleophiles to generate new carbon-carbon bonds. 08 xhese cations are formed as iron-alkene complexes, usually by reaction of cyclo-pentadienyl dicarbonyl ferrate anion (478) with an allylic halide such as 3-chloro-2-methyl-l-propene. The... 

Methaiiyi chioride(3-Chloro-2-methyl-l-propene) 72 1 4340 0 9475 Phthalimide deriv, 89-90... 

Chloro-2-methyl-l-propene,methallyl chloride, CH2=C(CH3)-CH2C1, is produced by the chlorination of isobutylene in the gas phase at temperatures below 100 C. Of greatest commercial interest are its reactions with sodium sulfite to give sodium methallyl sulfonate, and the production of 2-methyl epichlorohydrin. 

The ionization energies of the carbon-chlorine bond for (E)-l-chloro-2-butene and 3-chloro-2-methyl-l-propene in the gas phase are 672 and 706 kj mole", respectively. Using molecular orbital concepts, explain this energy difference based on the stability of the carbocations. 

Both compounds give allyl carbocations. One of the resonance contributors for the carbocation from (E)-l-chloro-2-butene has its positive charge at a secondary carbon atom. In terms of molecular orbital theory, the methyl group is at the end of an allyl system, where it affects the stability of the MO. The two resonance contributors for the carbocation from 3-chloro-2-methyl-l-propene are both primary. In terms of molecular orbital theory, the methyl group is bonded to the center carbon of an allyl system. There is a node at the C-2 of the Tt MO, and the methyl group cannot stabilize the carbocation. 

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