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All 3 posts Subject: phenylcyclopropane rearrangment rxns Please login to post Down

stratosphere
(Hive Bee)
03-09-04 20:59
No 494021
      phenylcyclopropane rearrangment rxns

after finding this convenient synthesis of phenylcyclopropane from cinnamdehyde and hydrazine:
http://www.orgsyn.org/orgsyn/prep.asp?prep=cv5p0929

i was looking for articles dealing with rearrangement reactions of this molecule to 1-phenyl-2-propene.

stratosphere
(Hive Bee)
03-10-04 00:14
No 494058
      with all due respect, i believe this post is...

with all due respect, i believe this post is of a wider scope then my mention of the pheynlcyclopropane synth in response to Post 461098 (Bwiti: "a-Methylstyrene Info..", Chemistry Discourse) , mainly because this extends to the synthesis of 1-phenyl-2-propene in addition to a-methylstyrene.
if i edit out the mention of a-methylstyrene and limit the discussion to 1-phenyl-2-propene, would it be possible to move it to the stimulants form and remove the cross-posted rating?

stratosphere
(Hive Bee)
03-11-04 20:39
No 494462
      the only info ive been able to find on this is

the only info ive been able to find on this is from my chem text, and basically states that cyclopropane undergoes isomerization to propene at 500C with a contact time of ~0.5s, it goes on to state that substituted cyclopropanes can undergo at sometimes much lower temps.
it does not state what solid phase catalysts aid in the isomerization.
(presumably this would carried out by running the vapor through a heated tube, which may or may not contain a catalyst)

due to the stabilizing influence of the phenyl group on a alpha-carbon radical, i would assume the predominate product would be 1-phenyl-1-propene especially if the temperature is kept as low as possible while still getting a resonable rate of isomerization,
the stabilizing influence of the phenyl group on isomerization intermediates (a-carbon radical) would also presumably lower the temp needed as compared to a alkyl substituted cyclopropane, however i cannot find good data for even simple alkylcyclopropanes.
the (newer) literature on cyclopropane isomerizations seems to focus on arcane aspects of photocatalyzed pericyclic reactions with YAG lasers etc, raman scattering, etc.

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	All 3 posts		Subject: phenylcyclopropane rearrangment rxns		Please login to post		Down


		stratosphere (Hive Bee) 03-09-04 20:59 No 494021				phenylcyclopropane rearrangment rxns
						after finding this convenient synthesis of phenylcyclopropane from cinnamdehyde and hydrazine: http://www.orgsyn.org/orgsyn/prep.asp?prep=cv5p0929 i was looking for articles dealing with rearrangement reactions of this molecule to 1-phenyl-2-propene.



		stratosphere (Hive Bee) 03-10-04 00:14 No 494058				with all due respect, i believe this post is...
						with all due respect, i believe this post is of a wider scope then my mention of the pheynlcyclopropane synth in response to Post 461098 (Bwiti: "a-Methylstyrene Info..", Chemistry Discourse) , mainly because this extends to the synthesis of 1-phenyl-2-propene in addition to a-methylstyrene. if i edit out the mention of a-methylstyrene and limit the discussion to 1-phenyl-2-propene, would it be possible to move it to the stimulants form and remove the cross-posted rating?



		stratosphere (Hive Bee) 03-11-04 20:39 No 494462				the only info ive been able to find on this is
						the only info ive been able to find on this is from my chem text, and basically states that cyclopropane undergoes isomerization to propene at 500C with a contact time of ~0.5s, it goes on to state that substituted cyclopropanes can undergo at sometimes much lower temps. it does not state what solid phase catalysts aid in the isomerization. (presumably this would carried out by running the vapor through a heated tube, which may or may not contain a catalyst) due to the stabilizing influence of the phenyl group on a alpha-carbon radical, i would assume the predominate product would be 1-phenyl-1-propene especially if the temperature is kept as low as possible while still getting a resonable rate of isomerization, the stabilizing influence of the phenyl group on isomerization intermediates (a-carbon radical) would also presumably lower the temp needed as compared to a alkyl substituted cyclopropane, however i cannot find good data for even simple alkylcyclopropanes. the (newer) literature on cyclopropane isomerizations seems to focus on arcane aspects of photocatalyzed pericyclic reactions with YAG lasers etc, raman scattering, etc.

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