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- Title
Cyclodiphosphazanes as synthetic probes: P-C/P-N bond formation from the reaction with functionalized propargyl alcohols and N-hydroxy substrates.
- Authors
GANGADHARARAO, G; KUMARA SWAMY, K
- Abstract
Phosphano-indoles were synthesized in a fairly straightforward route from the reaction of simple cyclodiphosphazanes [XP( μ-N- t-Bu)PY] [X = Y = NH- t-Bu ( 1a); X = Y = NH- i-Pr ( 1b)] with o-aminophenyl functionalized propargyl alcohols. The reaction occurs via an allene intermediate formed by P -O-C → P (O)-C rearrangement, followed by cyclization utilizing the central allenic carbon and the -NH functionality. In a similar way, cyclodiphosphazanes [XP( μ-N- t-Bu)PY] [X = Y = Cl ( 1c); X = Cl, Y = NH- t-Bu ( 1d)] have been treated with N-hydroxy substrates to obtain novel P -O-N → P (O)-N rearranged products. X-ray structures of the four products, 2-(1-phenyl-ethyl)-3-[( t-Bu)NH)P( μ-N- t-Bu)P(O)]-indole [ 14], cis-{[-C(=O)-C H-C(=O)-]-N-P(=O)-N- t-Bu} [ cis- 18], trans-{[-C(=O)-C H-C(=O)-]-N-P(=O)-N- t-Bu} [ trans- 18] and cis-[( t-BuNH)P( μ-N- t−Bu)P(=O)-N{ -C(=O)-CH-CH-C(=O)-}] [ cis- 19] are also reported. [Figure not available: see fulltext.]
- Subjects
PHOSPHAZANES; CHEMICAL bonds; PROPARGYL alcohol; INDOLE compounds; PHOSPHORUS compound synthesis; HYDROXY acids; SUBSTRATES (Materials science)
- Publication
Journal of Chemical Sciences, 2015, Vol 127, Issue 2, p197
- ISSN
0974-3626
- Publication type
Article
- DOI
10.1007/s12039-015-0772-7