𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Stereochemistry of the oxidative cleavage of palladium-carbon bonds by cupric chloride

✍ Scribed by Jan-E. Bäckvall

Publisher
Elsevier Science
Year
1977
Tongue
French
Weight
129 KB
Volume
18
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Oxidative cleavage of palladium-carbon bonds where a nucleophile replaces palladium (eq 1) occurs in catalytic systems utilizing palladium 2.3 and has recently been used to achieve oxy-

RuD ArCOzOH

HAH CH2C12 )

Acetoxypalladation of double bonds is known to be a trans-process.

12 Consequently, the cleavage of the palladium-carbon bond by cupric chloride at high chloride concentration takes place with inversion. This is in contrast to recent results that indicate a radical mechanism in the copper(X) cleavage of a palladium-carbon bond but is consistent with the idea 2c that oxidative cleavage occurs with predominant inversion in the presence of excess of free nucleophile.

Acknowledgement. The author thanks B. hermark and K.B. Sharpless for stimulating discussions and the American Scandinavian Foundation and Stiftelsen Blanceflor-Boncompagni Ludovisi f8dd Bildt for fellowships.

📜 SIMILAR VOLUMES

The oxidative cleavage of carbontin bon
The oxidative cleavage of carbontin bond catalyzed by heteropolyacids of molybdenum
✍ M.H Alizadeh; H Razavi; F.F Bamoharram; K Daneshvar 📂 Article 📅 2003 🏛 Elsevier Science 🌐 English ⚖ 164 KB

Heteropolymolybdoacids, H 3 [PMo 12 O 40 ] and H 6 [P 2 Mo 18 O 62 ], catalyze the oxidative cleavage of C-Sn bond in the organotin derivatives of dibenzyldichlorotin (1) and tribenzylchlorotin (2) in the presence of dioxygen. Benzaldehyde is the major reaction product, accompanied by smaller amount