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Today I read two publications stating that cyclopropane's ring can be opened by reactions of it with $\ce{Cl2/Br2/HCl/HBr}$. Correct me please if I interpreted something wrong.

Here are these publications:

  1. Lee, C. C.; Hahn, B.; Wan, K.; Woodcock, D. J. Reactions of cyclopropane with hydrochloric acid and of bromocyclopropane with hydrobromic acid. J. Org. Chem. 1969, 34 (10), 3210–3211. DOI: 10.1021/jo01262a097.

  2. Lambert, J. B.; Chelius, E. C.; Schulz, W. J.; Carpenter, N. E. Polar bromination and chlorination of cyclopropane. J. Am. Chem. Soc. 1990, 112 (8), 3156–3162. DOI: 10.1021/ja00164a043.

I read as well that cyclopropane has extra reactivity (due to ring strain obviously) so in the light, it behaves like a linear alkane getting substituted but in the absence of light, ring gets opened (as shown in a ChemGuide article.

Here are my questions about ring-strained cycloalkanes:

  • can be ring-opening agents for cyclopropane used for cyclobutane?
  • can we open ring-strained cycloalkanes with hydrogen (and catalyst of course)?
  • can we substitute cyclobutane like a cyclopropane? (in light)

But, still, I got a few questions about higher cycloalkanes' chemistry

  • does hydrogen with catalyst open higher cycloalkanes' rings?
  • in the reaction of $\ce{Cl2/Br2}$ with higher cycloalkanes ($n>4$), ring gets opened or compound is substituted?
  • do higher cycloalkanes ($n>4$) even react with $\ce{HCl/HBr}$?
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