10477-99-3Relevant articles and documents
Fluorous Mitsunobu reagents and reactions
Dandapani, Sivaraman,Curran, Dennis P.
, p. 3855 - 3864 (2002)
A fully fluorous Mitsunobu reaction procedure is introduced. This employs both existing [(C6F13CH2CH2C6H 4)2PPh] and new [C8F17CH2CH2C6H 4PPh2] fluorous phosphines and a new fluorous azodicarboxylate (C6F13CH2CH2OC(O)N=NCOOCH 2CH2C6F13). A procedure involving parallel reactions with representative nucleophiles and alcohols under typical Mitsunobu conditions in THF followed by rapid solid phase extraction (spe) over fluorous silica provides clean products in excellent yields. The fluorous fraction containing the oxidized phosphine oxide and the reduced hydrazide can be readily separated and the starting reagents can be regenerated by appropriate redox reactions in high yield for reuse.
Na2CO3/SOCl2: A mild and convenient reagent for the preparation of isopropyl carboxylates
Kazemi, Foad,Kiasat, Ali Reza,Mombaini, Began
, p. 1187 - 1191 (2004)
Na2CO3/SOCl2 has been used for esterification of aliphatic and aromatic acids with isopropanol. This esterification method is compatible with a wide assortment of functional groups.
Separation tagging with cyclodextrin-binding groups: Mitsunobu reactions with bis-(2-(1-adamantyl)ethyl) azodicarboxylate (BadEAD) and bis-(1-adamantylmethyl) azodicarboxylate (BadMAD)
Dandapani, Sivaraman,Newsome, Jeffery J.,Curran, Dennis P.
, p. 6653 - 6656 (2007/10/03)
A new method for separation tagging with cyclodextrin-binding groups is introduced and is exemplified in the context of the Mitsunobu reaction with adamantyl tags. HPLC experiments showed that molecules containing adamantyl groups were especially well retained on Sumichiral OA7500 β-methylated cyclodextrin bonded silica columns relative to many other types of molecules. Two new Mitsunobu reagents, bis-(1-adamantylmethyl) azodicarboxylate (BadMAD) and bis-(2-(1-adamantyl)ethyl) azodicarboxylate (BadEAD), were prepared, used in typical Mitsunobu reactions and separated with both β-methylated cyclodextrin bonded silica and standard silica.