Kinetic control in the formation of meso-dithia[3.3]-paracyclophane S,S′-dioxide |
| |
Authors: | Anna Barattucci Paola Bonaccorsi Teresa Papalia Nadia Manganaro Giuseppe Gattuso |
| |
Institution: | 1. Dipartimento di Scienze Chimiche, Università di Messina, Viale F. Stagno d’Alcontres 31, 98166 Messina, Italy;2. Dipartimento di Scienze del Farmaco e Prodotti per la Salute, Università di Messina, Villaggio SS. Annunziata, 98168 Messina, Italy |
| |
Abstract: | meso-(R,S)-Dithia3.3]-paracyclophane S,S′-dioxide is formed with complete stereoselection by the thermolysis of 3,3′-1,4-phenylene-bis(methylenesulfinyl)]-dipropanoate—that generates in situ two transient sulfenic acid functions—in the presence of p-diethynylbenzene. By employing an improved procedure that we have recently optimized, the title compound has been prepared in a 70% yield as a single diastereoisomer. A density functional B3LYP/6-311+G(d,p) study demonstrates that the final syn-addition cyclization step takes place under kinetic control, through a five-membered transition state that defines the stereochemistry of the resulting cyclophane. |
| |
Keywords: | KRDMVSVEZJYEBY-UHFFFAOYSA-N KRDMVSVEZJYEBY-UHFFFAOYSA-N KRDMVSVEZJYEBY-UHFFFAOYSA-N AXRTZYVMUPSSKX-UHFFFAOYSA-N AXRTZYVMUPSSKX-UHFFFAOYSA-N |
本文献已被 ScienceDirect 等数据库收录! |
|