ISSN:
1434-193X
Keywords:
Phosphanorbornadiene
;
Allylic metalation
;
Allylic bromination
;
BIPNOR dioxide
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
-3-Methyl-substituted 1-phosphanorbornadiene oxides or sulfides such as 1a,b are either metalated by a strong base (n-BuLi or LDA) or brominated by NBS at the methyl substituent. The reaction of the resulting delocalised carbanions 2a,b takes place either at C-2 (H+, MeI) or at the methylene group (Me3SiCl, ClPPh2, I2). In the last case, γ-functional (5a,b or 6a,b) or bridged (7) phosphanorbornadienes are obtained. Similarly, the reaction of 3-bromomethyl-1-phosphanorbornadiene oxides such as 8 with nucleophiles [NaCH(CO2Me)2, PhO-, Me2NH, PhCH2NH2] yields the corresponding γ-functional phosphanorbornadienes 9-12. This chemistry has also been applied to the BIPNOR dioxide 13.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
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