Abstract
By treatment at pH 9.5, starting from sulfonylurea (1f) (Rimsulfuron®), the diheteroaryl amine (3) is exclusively obtained, whereas under the same conditions sulfonylureas (1a-e) showed only cleavage of the SO2-NH bond. A reaction mechanism proceeding through a five-membered transition state was strongly suggested by both semiempirical and ab initio molecular orbital calculations.
| Original language | English |
|---|---|
| Pages (from-to) | 2517-2526 |
| Number of pages | 10 |
| Journal | Heterocycles |
| Volume | 53 |
| Issue number | 11 |
| Publication status | Published - Nov 1 2000 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
The cleavage of sulfonylurea herbicide Rimsulfuron® under basic conditions : A computational investigation. / Galeazzi, Roberta; Marucchini, Cesare; Orena, Mario; Porzi, Gianni.
In: Heterocycles, Vol. 53, No. 11, 01.11.2000, p. 2517-2526.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - The cleavage of sulfonylurea herbicide Rimsulfuron® under basic conditions
T2 - A computational investigation
AU - Galeazzi, Roberta
AU - Marucchini, Cesare
AU - Orena, Mario
AU - Porzi, Gianni
PY - 2000/11/1
Y1 - 2000/11/1
N2 - By treatment at pH 9.5, starting from sulfonylurea (1f) (Rimsulfuron®), the diheteroaryl amine (3) is exclusively obtained, whereas under the same conditions sulfonylureas (1a-e) showed only cleavage of the SO2-NH bond. A reaction mechanism proceeding through a five-membered transition state was strongly suggested by both semiempirical and ab initio molecular orbital calculations.
AB - By treatment at pH 9.5, starting from sulfonylurea (1f) (Rimsulfuron®), the diheteroaryl amine (3) is exclusively obtained, whereas under the same conditions sulfonylureas (1a-e) showed only cleavage of the SO2-NH bond. A reaction mechanism proceeding through a five-membered transition state was strongly suggested by both semiempirical and ab initio molecular orbital calculations.
UR - http://www.scopus.com/inward/record.url?scp=0034325908&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0034325908&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0034325908
VL - 53
SP - 2517
EP - 2526
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 11
ER -