Tetrahedron

Fluorous Mitsunobu reagents and reactions

S Dandapani, DP Curran

Index: Dandapani, Sivaraman; Curran, Dennis P. Tetrahedron, 2002 , vol. 58, # 20 p. 3855 - 3864

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Citation Number: 114

Abstract

A fully fluorous Mitsunobu reaction procedure is introduced. This employs both existing [( C6F13CH2CH2C6H4) 2PPh] and new [C8F17CH2CH2C6H4PPh2] fluorous phosphines and a new fluorous azodicarboxylate (C6F13CH2CH2OC (O) N NCOOCH2CH2C6F13). A procedure involving parallel reactions with representative nucleophiles and alcohols under typical Mitsunobu conditions in THF followed by rapid solid phase extraction (spe) over ...

 Related Synthetic Route
phthalimide Structure

136918-14-4

phthalimide

Isopropanol Structure

67-63-0

Isopropanol

~74%

2-Isopropyl-1H-isoindole-1,3(2H)-dione Structure

304-17-6

2-Isopropyl-1H-...

(4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl)diphenylphosphine oxide Structure

851869-38-0

(4-(3,3,4,4,5,5...

~%

[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]-diphenylphosphane Structure

462996-04-9

[4-(3,3,4,4,5,5...

Chlorodiphenylphosphine Structure

1079-66-9

Chlorodiphenylp...

~%

[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]-diphenylphosphane Structure

462996-04-9

[4-(3,3,4,4,5,5...

1-BROMO-4-(1H,1H,2H,2H-PERFLUOROPENTYL)BENZENE Structure

195324-88-0

1-BROMO-4-(1H,1...

~%

[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]-diphenylphosphane Structure

462996-04-9

[4-(3,3,4,4,5,5...

phthalimide Structure

136918-14-4

phthalimide

Ethanol Structure

64-17-5

Ethanol

~78%

n-ethylphthalimide Structure

5022-29-7

n-ethylphthalimide


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