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All 4 posts Subject: Secondary Amines via Alkyl Azides Please login to post Down

Rhodium
(Chief Bee)
11-24-03 09:04
No 472833
User Picture       Secondary Amines via Alkyl Azides
(Rated as: excellent)

This looks like a much more versatile and user-friendly route than the one posted in Post 210412 (foxy2: "MDE from Safrole Azide", Novel Discourse)
It also seems to be related to the procedure mentioned in Post 325198 (Ritter: "Azides--> N-Methylamines", Novel Discourse)

A Convergent One-Pot Synthesis of Secondary Amines via Aza-Wittig Reaction
Tadeusz Gajda, Anna Koziara, Krystyna Osowska-Pacewicka, Stefan Zawadzki, Andrzej Zwierzak
Synthetic Communications, 22(13), 1929-1938 (1992) (https://www.rhodium.ws/chemistry/aza-wittig.html)

Abstract
Secondary amines are obtained in moderate-good yields by reduction of crude imines prepared from N-alkyltriethoxyiminophosphoranes and aldehydes via the aza-Wittig reaction. N-Alkyltriethoxyiminophosphoranes are synthesized by one-pot azidation of alkyl bromides followed by Staudinger reaction.

Rhodium
(Chief Bee)
12-08-03 11:53
No 475410
User Picture       Another similar one-pot article
(Rated as: good read)

One-Pot Conversion Of Alkyl Bromides Into Imines Via The Staudinger Reaction
Petr Vanek & Petr Klán
Synth. Commun. 30(8), 1503-1507 (2000) (https://www.rhodium.ws/chemistry/aza-wittig.html#imine)

Abstract
A new one-pot procedure for transforming primary alkyl bromides into the corresponding imines via the Staudinger reaction has been developed. Acetonitrile was found to be an excellent solvent for azidation as well as the reaction of organic azide with triphenylphosphine and a carbonyl compound.

Rhodium
(Chief Bee)
10-02-04 19:19
No 534197
User Picture       One-Pot Aza-Wittig Based Route to Amines
(Rated as: excellent)

A One-Pot Aza-Wittig Based Solution and Polymer Supported Route to Amines
K. Hemming, M. J. Bevan, C. Loukou, S. D. Patel, D. Renaudeau
Synlett 1565-1568 (2000) (https://www.rhodium.ws/chemistry/aza-wittig.html#onepotpoly)

Abstract
This paper presents a high yielding one-pot solution phase and polymer supported synthesis of a range of primary and secondary amines starting from azides and aldehydes. The synthesis utilises a tandem process which begins with an aza-Wittig reaction between the aldehyde and an iminophosphorane, followed by reduction, or organometallic 1,2-addition reaction, of the resultant imine. The requisite iminophosphoranes were accessed using the highly efficient Staudinger reaction between the azide starting material and a phosphine. The process was applicable to the solid phase by the use of polymer supported iminophosphoranes and polymer supported cyanoborohydride.

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psychokitty
(«»)
10-05-04 02:25
No 534477
      Review of Azide Chemistry
(Rated as: excellent)

The following PDF is a review of Azide chemistry:

Azides: Their Preparation and Synthetic Uses
Eric F. V. Scriven & Kenneth Turnbull
Chemical Reviews, Vol. 88, No. 2, p. 297- (1988)

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	All 4 posts		Subject: Secondary Amines via Alkyl Azides		Please login to post		Down


		Rhodium (Chief Bee) 11-24-03 09:04 No 472833				Secondary Amines via Alkyl Azides (Rated as: excellent)
						This looks like a much more versatile and user-friendly route than the one posted in Post 210412 (foxy2: "MDE from Safrole Azide", Novel Discourse) It also seems to be related to the procedure mentioned in Post 325198 (Ritter: "Azides--> N-Methylamines", Novel Discourse) A Convergent One-Pot Synthesis of Secondary Amines via Aza-Wittig Reaction Tadeusz Gajda, Anna Koziara, Krystyna Osowska-Pacewicka, Stefan Zawadzki, Andrzej Zwierzak Synthetic Communications, 22(13), 1929-1938 (1992) (https://www.rhodium.ws/chemistry/aza-wittig.html) Abstract Secondary amines are obtained in moderate-good yields by reduction of crude imines prepared from N-alkyltriethoxyiminophosphoranes and aldehydes via the aza-Wittig reaction. N-Alkyltriethoxyiminophosphoranes are synthesized by one-pot azidation of alkyl bromides followed by Staudinger reaction.



		Rhodium (Chief Bee) 12-08-03 11:53 No 475410				Another similar one-pot article (Rated as: good read)
						One-Pot Conversion Of Alkyl Bromides Into Imines Via The Staudinger Reaction Petr Vanek & Petr Klán Synth. Commun. 30(8), 1503-1507 (2000) (https://www.rhodium.ws/chemistry/aza-wittig.html#imine) Abstract A new one-pot procedure for transforming primary alkyl bromides into the corresponding imines via the Staudinger reaction has been developed. Acetonitrile was found to be an excellent solvent for azidation as well as the reaction of organic azide with triphenylphosphine and a carbonyl compound.



		Rhodium (Chief Bee) 10-02-04 19:19 No 534197				One-Pot Aza-Wittig Based Route to Amines (Rated as: excellent)
						A One-Pot Aza-Wittig Based Solution and Polymer Supported Route to Amines K. Hemming, M. J. Bevan, C. Loukou, S. D. Patel, D. Renaudeau Synlett 1565-1568 (2000) (https://www.rhodium.ws/chemistry/aza-wittig.html#onepotpoly) Abstract This paper presents a high yielding one-pot solution phase and polymer supported synthesis of a range of primary and secondary amines starting from azides and aldehydes. The synthesis utilises a tandem process which begins with an aza-Wittig reaction between the aldehyde and an iminophosphorane, followed by reduction, or organometallic 1,2-addition reaction, of the resultant imine. The requisite iminophosphoranes were accessed using the highly efficient Staudinger reaction between the azide starting material and a phosphine. The process was applicable to the solid phase by the use of polymer supported iminophosphoranes and polymer supported cyanoborohydride. ^{The Hive - Clandestine Chemists Without Borders}



		psychokitty («») 10-05-04 02:25 No 534477				Review of Azide Chemistry (Rated as: excellent)
						The following PDF is a review of Azide chemistry: Azides: Their Preparation and Synthetic Uses Eric F. V. Scriven & Kenneth Turnbull Chemical Reviews, Vol. 88, No. 2, p. 297- (1988)

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