Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/wiley/phosphorylation-of-n-iso-propyl-and-n-tert-butylpyrroles-with-pOyEEugkcL
References (15)
-
Olga Carmona, R. Greenhouse, R. Landeros, J. Muchowski (1980)
Synthesis and rearrangement of 2-(arylsulfinyl)- and 2-(alkylsulfinyl)pyrrolesJournal of Organic Chemistry, 45
-
H. Anderson, L. Hopkins (1966)
PYRROLE CHEMISTRY: V. FRIEDEL–CRAFTS ISOPROPYLATIONS OF SOME PYRROLE DERIVATIVESCanadian Journal of Chemistry, 44
-
W. Davies, A. Pinder, I. Morris (1962)
The synthesis and resolution of (±)-tropan-2-oneTetrahedron, 18
-
M. Kakushima, R. Frenette (1984)
Synthesis of pyrrolyl sulfidesJournal of Organic Chemistry, 49
-
P. Politzer, H. Weinstein (1975)
Molecular electrostatic potentials-II: Mechanistic aspects of electrophilic interactions of some five-membered heterocyclesTetrahedron, 31
-
F. Cordell, J. Boggs (1981)
Structure and degree of aromatic character in furan, pyrrole, and thiopheneJournal of Molecular Structure-theochem, 85
-
H. Anderson, C. Huang (1967)
Pyrrole chemistry. VI. Syntheses and electrophilic substitution reactions of some 3-substituted pyrrolesCanadian Journal of Chemistry, 45
-
S. Ivonin, A. Tolmachev, A. Pinchuk (2002)
C‐phosphorylation of N‐arylpyrrolesHeteroatom Chemistry, 13
-
H. Anderson, L. Hopkins (1964)
PYRROLE CHEMISTRY: III. FRIEDEL-CRAFTS ISOPROPYLATION OF METHYL 2-PYRROLECARBOXYLATECanadian Journal of Chemistry, 42
-
R. Olsen, H. Snyder (1963)
Concerning the Position of Thiocyanation in Pyrrole1Journal of Organic Chemistry, 28
-
M. Majchrzak, G. Simchen (1986)
β-silylation of N-alkylpyrroles, experimental support of theoretical calculationsTetrahedron, 42
-
A. Tolmachev, S. Ivonin, A. Pinchuk (1995)
Phosphorylation of five‐membered aromatic heterocycles with phosphorus tribromideHeteroatom Chemistry, 6
-
C. Candy, R. Jones, P. Wright (1970)
Pyrrole studies. Part XV. Vilsmeier–Haack formylation of 1-substituted pyrrolesJournal of The Chemical Society C: Organic
-
S. Ivonin, Tatjana Terikovska, A. Chaikovskaya, A. Marchenko, Georgiy Koydan, A. Pinchuk, A. Tolmachev (1999)
C‐phosphorylation of n‐methylpyrroleHeteroatom Chemistry, 10
-
Javier DeSales, R. Greenhouse, J. Muchowski (1982)
Synthesis and rearrangement of pyrrolyl sulfides and sulfonesJournal of Organic Chemistry, 47
- Publisher
- Wiley
- Copyright
- Copyright © 2005 Wiley Periodicals, Inc.
- ISSN
- 1042-7163
- eISSN
- 1098-1071
- DOI
- 10.1002/hc.20158
- Publisher site
- See Article on Publisher Site
Abstract
The investigation concerns the effect of a bulky substituent at the pyrrole nitrogen atom on the orientation and regioselectivity of pyrrole phosphorylation with phosphorus(III) halides. As shown, phosphorylation of N‐iso‐propylpyrrole with phosphorus tribromide or trichloride proceeds nonregioselectively at positions 2 and 3 but it is followed by the 2 → 3 migration of the dihalogenophosphine group which quantitatively yields the 3‐isomer. N‐tert‐butylpyrrole is regioselectively phosphorylated with halogenophosphines at position 3. The tert‐butyl substituent at the nitrogen atom does not preclude the binding of even two or three pyrrolyl residues to the phosphorus atom. The key compounds, 3‐pyrrolyldihalogenophosphines, were isolated in a pure state, characterized and used to obtain a number of stable phosphorus(V) derivatives. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:599–604, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20158
Journal
Heteroatom Chemistry – Wiley
Published: Jan 1, 2005