4- Chloro-2-heptene

Benz-7-azabicyclo[2.2.1]heptenes in isoindole synthesis, 4, 351 Benz[e][l, 2]azaborine, 2-chloro-1,2-dihydro-synthesis, 1, 647... 

Hemimellitene, 34, 56 Hendecynoic ACID, 32, 104 m-Heptamide, 37, 50 w-Heptanoic acid, 37, 50 1-HEPTEN-3-ONE, 1-CHLORO-6-METHYL-,... 

Recently, Malpass et al. reported a synthesis of epibatidine isomers also under reductive Heck conditions [134, 135]. 2-Azabicyclo[2.2.1]heptene 167 was assembled by cycloaddition of an iminium salt with cyclopentadiene. Treatment of 167 with 2-chloro-5-iodopyridine provided a mixture of exo-5-(6-chloro-3-pyridyl) derivative 168 and exo-6-(6-chloro-3-pyridyl) derivative 169. 

A facile intramolecular carbomagnesiation becomes possible by inserting one more carbon between the reactive magnesium center and the double bond. For example, when a 6-chloro-l-heptene was refluxed with magnesium, 1,2-dimethylcyclopentane (cis/trans = ca 1/4) was obtained in 88% yield after hydrolysis (Scheme 47) °. The cyclization shows a 5-exo-trig selectivity and the product derived from 6-endo-trig cyclization (methylcyclohexane) is not observed. 

Problem 6.6 Write structural formulas for (a) ( )-2-methyl-3-hexene trans), b) (S)-3-chloro-l-pentene, (c) (R),(Z)-2-chloro-3-heptene (c/s). 

When the reaction was performed with a tertiary chloride that has a radical probe, such as 6-chloro-6-methyl-l-heptene (64), the only product found was the rearranged phosphine 65, isolated in 43% yield (equation 58). 

Bicyclo[2.2.1]heptene 5-Chloro-5-cyan-7-fluoro- E10 (5-Ti —cyclo-pentadien + En/N—F-Comp.)... 

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