Abstract
A literature review of the major stoichiometric uses of tertiary
phosphines, with particular emphasis on the relative abilities of
trialkylphosphines and triarylphosphines in Wittig, Staudinger,
or Mitsunobu reactions, is presented. Pronounced differences in
reaction rates and selectivity, product yields and ease of by-product
removal are often observed when trialkylphosphines are compared
with triarylphosphines as promoters in these types of reactions.
Also presented here is a compilation of some useful physical properties
for selected trialkylphosphines, their usual methods of preparation
and typical uses in organic synthesis.
1 Introduction
2 Wittig Reaction
2.1 Staudinger Reaction
3 Hydroxyl Replacement Reaction
3.1 Mitsunobu Reaction
3.2 Tertiary Phosphines with Organosulfur and Organoselenium
Compounds
3.3 Nitro Compounds and Nitriles
3.4 Reactions with Organic Halides
4 Reactions Catalyzed by Trialkylphosphines
5 Michael Reaction
6 Conclusions
Key words
phosphorus - Mitsunobu - Wittig Reactions - nucleophiles - cleavage
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