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All 2 posts Subject: Cyclobutanone -> GBL idea. Please login to post Down

Novice
(Hive Bee)
11-01-04 17:47
No 539092
Cyclobutanone -> GBL idea.

I know how you people feel about grand ideas without any decent references or empirical basis... Well, deal with it ;)

I was looking at the Baeyer-Villiger rearrangement/oxidation and started wondering why it should'nt be applicable on cyclobutanone to yield GBL.

Vogel's 5th ed. (p. 728) states the following concerning the formation of lactones via the Baeyer-Villiger rearrangement:

"Thus, m-chloroperbenzoic acid is used with many cyclic ketones although the time of reaction increases with ring size."

If this rule of thumb doesn't only apply on the use of m-chloroperbenzoic acid, and considering the ring size of cyclobutanone, the reaction should be pretty damn rapid.

Jerry March, in his book "Advanced organic chemistry 4th ed.", mentions for instance perbenzoic acid, or peracetic acid as examples of peracids that can be used, and that peroxytrifluoroacetic acid is particularly good for this purpose. The first two are very easily prepared in vivo as we all know, and cheap as well...

I have UTFSE and found nothing on this topic, and would like some comments from the more knowledgable bees.

Regards,
Novice

Rhodium
(Chief Bee)
11-01-04 18:26
No 539096
User Picture My past posts on this topic can be found like this

UTFSE for "cyclobutanone $"

^{The Hive - Clandestine Chemists Without Borders}

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	All 2 posts		Subject: Cyclobutanone -> GBL idea.		Please login to post		Down


		Novice (Hive Bee) 11-01-04 17:47 No 539092				Cyclobutanone -> GBL idea.
						I know how you people feel about grand ideas without any decent references or empirical basis... Well, deal with it ;) I was looking at the Baeyer-Villiger rearrangement/oxidation and started wondering why it should'nt be applicable on cyclobutanone to yield GBL. Vogel's 5th ed. (p. 728) states the following concerning the formation of lactones via the Baeyer-Villiger rearrangement: "Thus, m-chloroperbenzoic acid is used with many cyclic ketones although the time of reaction increases with ring size." If this rule of thumb doesn't only apply on the use of m-chloroperbenzoic acid, and considering the ring size of cyclobutanone, the reaction should be pretty damn rapid. Jerry March, in his book "Advanced organic chemistry 4th ed.", mentions for instance perbenzoic acid, or peracetic acid as examples of peracids that can be used, and that peroxytrifluoroacetic acid is particularly good for this purpose. The first two are very easily prepared in vivo as we all know, and cheap as well... I have UTFSE and found nothing on this topic, and would like some comments from the more knowledgable bees. Regards, Novice



		Rhodium (Chief Bee) 11-01-04 18:26 No 539096				My past posts on this topic can be found like this
						UTFSE for "cyclobutanone $" ^{The Hive - Clandestine Chemists Without Borders}

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