>> The reaction has been applied in the synthesis of aryl ethers. If you do not receive an email within 10 minutes, your email address may not be registered,
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>> The full text of this article hosted at iucr.org is unavailable due to technical difficulties. << >>
<< <]>> /Type /Page 0000006206 00000 n A detailed mechanism illustrating the Mitsunobu reaction in which one of the reacting compounds is an aromatic alcohol.
endobj /Contents 28 0 R 4 0 obj The nucleophile employed should be acidic, since one of the reagents ( DEAD , diethylazodicarboxylate) must be protonated during the course of the reaction to prevent from side reactions. trailer /Resources 29 0 R �_�m�s����L��b�q��x�R6��5]�A�˒�9C���u��wS��%�2��N�bo�RQ?���YA�I��w0g�Ӻf4"�{�6/�����;�l�uQS�9��Èm�啚�-��=�c�/�Cn�Y�1��]���*ڣ-���$�[ȷ3@�E����������s����gZ�8����&}9ā�J#&�Vr���Z����亨X /Parent 5 0 R >> The Mitsunobu reaction is a widely used and versatile method for the dehydrative oxidation–reduction condensation of an acid/pronucleophile usually with a primary or secondary alcohol that requires the combination of a reducing phosphine reagent together with an oxidizing azo reagent. 8 0 obj 0000002439 00000 n xref This intermediate then deprotonates the acidic compound to …
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<< Research Articles New Mitsunobu Reagents | TCI /Contents 26 0 R /Contents 20 0 R
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Chem. /PXCViewerInfo (PDF-XChange Viewer;2.5.193.0;Feb 15 2011;21:26:46;D:20130501141725+09'00') 0000001987 00000 n /Resources 21 0 R sI���t�K�LL�X� �d�.d����5���/d2���Z�.����\03dw\ g�������9jƭ�WNu�N�I.����w-�,rQfX�R1�-֔���� /Thumb 17 0 R /Contents 32 0 R /ModDate (D:20130501141725+09'00') endstream x�b```f``�������� �� �@���! Unlimited viewing of the article PDF and any associated supplements and figures. << /Parent 5 0 R /Parent 5 0 R The Mitsunobu reaction is a widely used and versatile method for the dehydrative oxidation–reduction condensation of an acid/pronucleophile usually with a primary or secondary alcohol that requires the combination of a reducing phosphine reagent together with an oxidizing azo reagent.
If you have previously obtained access with your personal account, please log in. /Parent 6 0 R /Subtype /XML 0000001359 00000 n
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/Contents 18 0 R /Type /Pages On the contrary, in the case of the reaction of less acidic HA, the hydrazo anion 4 attacks the alkoxyphosphonium 5 endobj /Producer (Acrobat Distiller 2.1 for Power Macintosh) and you may need to create a new Wiley Online Library account. endobj /Creator (Adobe PageMaker 6.0J)
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1 0 obj >> ��))��!��p�9 #�: >�����Uȹ��v"'��� �(� �H�9��p����0��/�� &/o��rRA��aIh����@Y�x[P�`l /Type /Page >> Both aliphatic alcohols and benzyl alcohols are suitable substrates for C–N bond construction.
Mitsunobu reaction and its application By Mohammad Mohsin Qadri 1 2. /Contents 24 0 R 13 0 obj The alcohol binds to the nucleophile and phosphonium ion to perform \(S_{N}2\) to yield the final substitution product.
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<< The mechanism begins by forming a zwitter ionic intermediate on DEAD by an action of \(PPh_{3}\). 0000064413 00000 n
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Unlimited viewing of the article/chapter PDF and any associated supplements and figures. /Title (Research Articles New Mitsunobu Reagents | TCI) endobj endstream /Resources 25 0 R 0000003289 00000 n 0000000016 00000 n /Parent 6 0 R +�{a��� i�~��2X@iA�:A��CXu�7@@�@\M(���P)�P%;��JI�,/d��4�ޠigdԧ �% �( ��9���C O�� ��Hv*����R��D'
>> Since its discovery in 1967 by Professor Oyo Mitsunobu (1934-2003),1,2 this reaction has enjoyed a privileged role in organic synthesis and medicinal chemistry because of its scope, stereospeci-ficity, and mild reaction conditions.
/Type /Catalog >> 384 0 obj <> endobj %���� 123 (2001) 9465-9467 /CreationDate (D:20050628203016+09'00')
Learn about our remote access options, Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China, Fax: (+852) 285‐71‐586. /Parent 3 0 R
>> Several important variations were discovered by Mitsunobu and his co-workers /Count 10 /Count 6 /Resources 19 0 R >> The utility of this reaction stems from the fact that it is generally highly stereoselective and occurs with inversion of the stereochemical configuration of the alcohol starting material.
View the article PDF and any associated supplements and figures for a period of 48 hours. endobj >> Working off-campus? endobj
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%%EOF 15 0 obj FLOW OF CONTENT Introduction Mechanism Recent advances Applications 1934-2003 – Esterification Work at the Aoyama Gakuin University, – Etherification Tokoyo. /Kids [7 0 R 8 0 R 9 0 R 10 0 R 11 0 R 12 0 R] The desired Mitsunobu reaction proceeds probably through the generally accepted path a shown in Scheme 4.2) number 123 Scheme 4. Please check your email for instructions on resetting your password. /Type /Metadata
/Kids [13 0 R 14 0 R 15 0 R 16 0 R]
/Count 4 /Type /Page
0000000616 00000 n /Type /Pages endobj Furthermore, as carboxylic acids, phenols, imides, sulfonamides, and other compounds can be used as the acid/pronucleophile, this reaction is useful for the preparation of a wide variety of functional groups. �0�(��+� !�0��n�K��!�RL��A+���, Research Articles New Mitsunobu Reagents | TCI. endobj
Mitsunobu Reaction The Mitsunobu Reaction allows the conversion of primary and secondary alcohols to esters, phenyl ethers, thioethers and various other compounds.