Hive Novel Discourse

	Main Index Search Register Login Who's Online FAQ Links
	Main Index Search Register Login Who's Online FAQ Links

	1 Online, 0 Active		You are not logged in

This is a historical archiveThe forum is read-only. Private information has been removed. It is not possible to login.

	Novel Discourse

All 10 posts Subject: P2P Please login to post Down

obituary
(Hive Addict)
08-13-01 21:38
No 204255
      P2P

Yes, obit is trying yet again for the new synth. now please say something and give refs if this has been seen before. obit knows that (believe it was) Rev. drone proposed a phenyllithium and bromoacetone synth for P2P.

does it work? (side question)

on to the new synth possibility:

triphenylborane + bromoacetone -(OH^-)-> P2P

this seems very reasonable considering that alkylboranes will react with bromo-keto comps to give ketones under basic conditions

how available is triphenylborane?

obituary
(Hive Addict)
08-14-01 18:02
No 204493
      Re: P2P

somebody?

PrimoPyro
(Newbee)
08-15-01 05:33
No 204702
      Re: P2P

i dunno about the theory, but as for availability:

triphenylborane: (C6H5)3B   CAS# 960-71-4
Crystalline, m.p. 147 deg C   b.p. 208 deg C/14mm

97.8% assay: 1g $17.50 5g $63.90   25g $278

from a wellknown global chemical manufacturer....
Of COURSE we don't know what we're doing! That's why it's called research! (boom...)    :)

jim
(Hive Bee)
08-15-01 14:01
No 204761
      Re: P2P

There is no reason why the enolate synhtesis shouldn't work.

I don't know about the borane synthesis however...

obituary
(Hive Addict)
08-15-01 14:34
No 204767
      Re: P2P

the only possible reason obit has found why the borane synth won't work is that the borane is directly attached to an aromatic. at the same time, obit doesn't think that it makes a difference in this case. it might if there were substitutions on the ring, but there aren't.   does anybody have a way to try this small scale/lab research on precursors, coughRHODIUMcough. damn cold.

lugh
(Hive Bee)
08-15-01 15:41
No 204789
      Re: P2P

These borane syntheses and the related nitrile syntheses are old and well known to many. Some other related refs are JACS 90: 5280,5936 & 6891 (1968) & 91: 4304, 6852 & 6854 Diazoeacetone can be used as an alternative to bromoacetone. They work very well with the substituted aromatics. While not the cheapest, these routes offer the advantage of being generally applicable, and thus very suited for our purposes.

obituary
(Hive Addict)
08-15-01 15:57
No 204793
User Picture       Re: P2P

do these work for the substituted aromatics? (please say yes, please say yes, please.....)

Rhodium
(Chief Bee)
08-15-01 16:42
No 204801
      Re: P2P

I have no facilities to run reactions like that. I'm just an information collector.

obituary
(Hive Addict)
08-15-01 16:46
No 204804
User Picture       Re: P2P

thanks anyways.

Rhodium
(Chief Bee)
08-16-03 02:07
No 453831
      Synthesis of ketones (P2P) via alkylboranes
(Rated as: excellent)

Here are all the references listed in Post 204789 (lugh: "Re: P2P", Novel Discourse) for the synthesis of different alkylboranes, as well as their further manipulation to ketones (like P2P/MDP2P). Check out the last two in particular if all of these articles overwhelm you.

Cyclic hydroboration of 1,5-cyclooctadiene. A simple synthesis of 9-borabicyclo[3.3.1]nonane, an unusually stable dialkylborane
Evord F. Knights, Herbert C. Brown
J. Am. Chem. Soc. 90(19), 5280-5281 (1968) (https://www.rhodium.ws/pdf/organoborane2ketone-1.pdf)

The reaction of trialkylboranes with diazoacetone. A new ketone synthesis
John Hooz, Siegfried Linke
J. Am. Chem. Soc. 90(21), 5936-5937 (1968) (https://www.rhodium.ws/pdf/organoborane2ketone-2.pdf)

Alkylation of diazoacetonitrile and ethyl diazoacetate by organoboranes. Synthesis of nitriles and esters
John Hooz, Siegfried Linke
J. Am. Chem. Soc. 90(24), 6891-6892 (1968) (https://www.rhodium.ws/pdf/organoborane2ketone-3.pdf)

Reaction of ethyl haloacetates and .alpha.-bromo ketones with B-aryl-9-borabicyclo(3.3.1)nonanes under the influence of potassium tert-butoxide. A new convenient procedure for the .alpha.-arylation of ketones and esters
Herbert Charles Brown, Milorad M. Rogic
J. Am. Chem. Soc. 91(15), 4304-4305 (1969) (https://www.rhodium.ws/pdf/organoborane2ketone-4.pdf)

Reaction of organoboranes with bromoacetone under the influence of potassium 2,6-Di-tert-butylphenoxide.
A convenient procedure for the conversion of olefins into methyl ketones via hydroboration
Herbert Charles Brown, Hirohiko Nambu, Milorad M. Rogic
J. Am. Chem. Soc. 91(24), 6852-6854 (1969) (https://www.rhodium.ws/pdf/organoborane2ketone-5.pdf)

Reaction of organoboranes with chloroacetonitrile under the influence of potassium 2,6-Di-tert-butylphenoxide.
A convenient procedure for the conversion of olefins into nitriles via hydroboration
Herbert Charles Brown, Hirohiko Nambu, Milorad M. Rogic
J. Am. Chem. Soc. 91(24), 6854-6855 (1969) (https://www.rhodium.ws/pdf/organoborane2ketone-6.pdf)

	https://the-hive.archive.erowid.org	the-hive@erowid.org



Powdered by the Necronomicon^TM v.4.8.1, © 2014 - 2016, KarmaSoft Systems Unlimited Europe. Patents pending. All rights reserved.
Links Erowid Rhodium


		obituary (Hive Addict) 08-13-01 21:38 No 204255				P2P
						Yes, obit is trying yet again for the new synth. now please say something and give refs if this has been seen before. obit knows that (believe it was) Rev. drone proposed a phenyllithium and bromoacetone synth for P2P. does it work? (side question) on to the new synth possibility: triphenylborane + bromoacetone -(OH^-)-> P2P this seems very reasonable considering that alkylboranes will react with bromo-keto comps to give ketones under basic conditions how available is triphenylborane?



		obituary (Hive Addict) 08-14-01 18:02 No 204493				Re: P2P
						somebody?



		PrimoPyro (Newbee) 08-15-01 05:33 No 204702				Re: P2P
						i dunno about the theory, but as for availability: triphenylborane: (C6H5)3B CAS# 960-71-4 Crystalline, m.p. 147 deg C b.p. 208 deg C/14mm 97.8% assay: 1g $17.50 5g $63.90 25g $278 from a wellknown global chemical manufacturer.... Of COURSE we don't know what we're doing! That's why it's called research! (boom...) :)



		jim (Hive Bee) 08-15-01 14:01 No 204761				Re: P2P
						There is no reason why the enolate synhtesis shouldn't work. I don't know about the borane synthesis however...



		obituary (Hive Addict) 08-15-01 14:34 No 204767				Re: P2P
						the only possible reason obit has found why the borane synth won't work is that the borane is directly attached to an aromatic. at the same time, obit doesn't think that it makes a difference in this case. it might if there were substitutions on the ring, but there aren't. does anybody have a way to try this small scale/lab research on precursors, coughRHODIUMcough. damn cold.



		lugh (Hive Bee) 08-15-01 15:41 No 204789				Re: P2P
						These borane syntheses and the related nitrile syntheses are old and well known to many. Some other related refs are JACS 90: 5280,5936 & 6891 (1968) & 91: 4304, 6852 & 6854 Diazoeacetone can be used as an alternative to bromoacetone. They work very well with the substituted aromatics. While not the cheapest, these routes offer the advantage of being generally applicable, and thus very suited for our purposes.



		obituary (Hive Addict) 08-15-01 15:57 No 204793				Re: P2P
						do these work for the substituted aromatics? (please say yes, please say yes, please.....)



		Rhodium (Chief Bee) 08-15-01 16:42 No 204801				Re: P2P
						I have no facilities to run reactions like that. I'm just an information collector.



		obituary (Hive Addict) 08-15-01 16:46 No 204804				Re: P2P
						thanks anyways.



		Rhodium (Chief Bee) 08-16-03 02:07 No 453831				Synthesis of ketones (P2P) via alkylboranes (Rated as: excellent)
						Here are all the references listed in Post 204789 (lugh: "Re: P2P", Novel Discourse) for the synthesis of different alkylboranes, as well as their further manipulation to ketones (like P2P/MDP2P). Check out the last two in particular if all of these articles overwhelm you. Cyclic hydroboration of 1,5-cyclooctadiene. A simple synthesis of 9-borabicyclo[3.3.1]nonane, an unusually stable dialkylborane Evord F. Knights, Herbert C. Brown J. Am. Chem. Soc. 90(19), 5280-5281 (1968) (https://www.rhodium.ws/pdf/organoborane2ketone-1.pdf) The reaction of trialkylboranes with diazoacetone. A new ketone synthesis John Hooz, Siegfried Linke J. Am. Chem. Soc. 90(21), 5936-5937 (1968) (https://www.rhodium.ws/pdf/organoborane2ketone-2.pdf) Alkylation of diazoacetonitrile and ethyl diazoacetate by organoboranes. Synthesis of nitriles and esters John Hooz, Siegfried Linke J. Am. Chem. Soc. 90(24), 6891-6892 (1968) (https://www.rhodium.ws/pdf/organoborane2ketone-3.pdf) Reaction of ethyl haloacetates and .alpha.-bromo ketones with B-aryl-9-borabicyclo(3.3.1)nonanes under the influence of potassium tert-butoxide. A new convenient procedure for the .alpha.-arylation of ketones and esters Herbert Charles Brown, Milorad M. Rogic J. Am. Chem. Soc. 91(15), 4304-4305 (1969) (https://www.rhodium.ws/pdf/organoborane2ketone-4.pdf) Reaction of organoboranes with bromoacetone under the influence of potassium 2,6-Di-tert-butylphenoxide. A convenient procedure for the conversion of olefins into methyl ketones via hydroboration Herbert Charles Brown, Hirohiko Nambu, Milorad M. Rogic J. Am. Chem. Soc. 91(24), 6852-6854 (1969) (https://www.rhodium.ws/pdf/organoborane2ketone-5.pdf) Reaction of organoboranes with chloroacetonitrile under the influence of potassium 2,6-Di-tert-butylphenoxide. A convenient procedure for the conversion of olefins into nitriles via hydroboration Herbert Charles Brown, Hirohiko Nambu, Milorad M. Rogic J. Am. Chem. Soc. 91(24), 6854-6855 (1969) (https://www.rhodium.ws/pdf/organoborane2ketone-6.pdf)

All 10 posts	End of thread	Top