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Reaction of arylenedioxytrihalophosphoranes with acetylenes 12. Alkylacetylenes in the reaction with 2,2,2-trihalobenzo-1,3,2-dioxaphospholes.
- Source :
- Russian Chemical Bulletin; Jan2014, Vol. 63 Issue 1, p149-177, 29p
- Publication Year :
- 2014
-
Abstract
- A reaction of 2,2,2-trihalobenzo-1,3,2-dioxaphospholes with terminal alkylacetylenes proceeds under mild conditions (∼20 °C) and leads to the formation of 4-alkylbenzo[ e]-1,2-oxaphosphinine 2-oxide derivatives. The presence of aliphatic substituents in acetylene decreases (as compared to their aromatic counterparts described earlier) regioselectivity of halogenation of benzo fragment in 4-alkylbenzo[ e]-1,2-oxaphosphinines: besides predominant 4-alkyl-2,6-dihalobenzo[ e]-1,2-oxaphosphinines, minor 2,7- and 2,8-dihalo-substituted 4-alkylbenzo[ e]-1,2-oxaphosphinines are formed. An unusual thermal isomerization of 4-alkyl-2-fluorobenzo[ e]-1,2-oxaphosphinines to 4-alkylidene-2-fluoro-3,4-dihydrobenzo[ e]-1,2-oxaphosphinines was discovered. Molecular and supramolecular structures of some 4-alkylbenzo[ e]-1,2-oxaphosphinines were studied by X-ray diffraction analysis. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 10665285
- Volume :
- 63
- Issue :
- 1
- Database :
- Complementary Index
- Journal :
- Russian Chemical Bulletin
- Publication Type :
- Academic Journal
- Accession number :
- 97808569
- Full Text :
- https://doi.org/10.1007/s11172-014-0409-x