Abstract
The reactions of 2-alkoxy-1,3,2-dioxaphospholane 2-oxide with various nucleophiles were studied both experimentally and theoretically. These studies show that 5-membered ring phosphate triesters act as ambident electrophiles: hard and bulky nucleophiles attack at the phosphorus while soft nucleophiles attack at the ring carbon.
| Original language | English |
|---|---|
| Pages (from-to) | 420-424 |
| Number of pages | 5 |
| Journal | Phosphorus, Sulfur and Silicon and the Related Elements |
| Volume | 183 |
| Issue number | 2-3 |
| DOIs | |
| Publication status | Published - Feb 2008 |
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Keywords
- 2-Alkoxy-1,3,2-dioxaphospholane 2-oxide
- Electrophilicity
- Hard and soft nucleophiles
- Steric bulk
ASJC Scopus subject areas
- Inorganic Chemistry
Cite this
Ambident electrophilicity of 5-membered ring phosphate triesters. / Ashkenazi, Nissan; Segall, Yoffi; Karton, Yishai; Zade, Sanjio S.; Bendikov, Michael.
In: Phosphorus, Sulfur and Silicon and the Related Elements, Vol. 183, No. 2-3, 02.2008, p. 420-424.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Ambident electrophilicity of 5-membered ring phosphate triesters
AU - Ashkenazi, Nissan
AU - Segall, Yoffi
AU - Karton, Yishai
AU - Zade, Sanjio S.
AU - Bendikov, Michael
PY - 2008/2
Y1 - 2008/2
N2 - The reactions of 2-alkoxy-1,3,2-dioxaphospholane 2-oxide with various nucleophiles were studied both experimentally and theoretically. These studies show that 5-membered ring phosphate triesters act as ambident electrophiles: hard and bulky nucleophiles attack at the phosphorus while soft nucleophiles attack at the ring carbon.
AB - The reactions of 2-alkoxy-1,3,2-dioxaphospholane 2-oxide with various nucleophiles were studied both experimentally and theoretically. These studies show that 5-membered ring phosphate triesters act as ambident electrophiles: hard and bulky nucleophiles attack at the phosphorus while soft nucleophiles attack at the ring carbon.
KW - 2-Alkoxy-1,3,2-dioxaphospholane 2-oxide
KW - Electrophilicity
KW - Hard and soft nucleophiles
KW - Steric bulk
UR - http://www.scopus.com/inward/record.url?scp=45849123912&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=45849123912&partnerID=8YFLogxK
U2 - 10.1080/10426500701735452
DO - 10.1080/10426500701735452
M3 - Article
VL - 183
SP - 420
EP - 424
JO - Phosphorus, Sulfur and Silicon and the Related Elements
JF - Phosphorus, Sulfur and Silicon and the Related Elements
SN - 1042-6507
IS - 2-3
ER -