✦ LIBER ✦

Reaction of 3-trimethylsilyloxy-2-aza-1,3-dienes with zirconocene: a transition metal promoted retro-Brook rearrangement

✍ Scribed by Vincent Gandon; Philippe Bertus; Jan Szymoniak

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 109 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00333-6

No coin nor oath required. For personal study only.

✦ Synopsis

2-Aza-1,3-dienes bearing trimethylsilyloxy group at C3 undergo an unusual zirconium-mediated retro-Brook rearrangement to produce, after hydrolysis, silylated amides. Both [1,3]-and [1,4]-oxygen to carbon silyl migrations are observed depending on the substrate structure.

📜 SIMILAR VOLUMES

New Transformations from a 3-Silyloxy 2-

New Transformations from a 3-Silyloxy 2-Aza-1,3-diene: Consecutive Zr-Mediated Retro-Brook Rearrangement and Reactions with Electrophiles

✍ Vincent Gandon; Philippe Bertus; Jan Szymoniak 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 118 KB

AbstractÐA one-pot procedure for the transformation of the title compound to a-functionalized (silylated) and a,b-unsaturated secondary amides was described. The following steps were involved: a Zr-mediated retro-Brook rearrangement, selective deprotonation with n-BuLi on the organometallic intermed

ChemInform Abstract: New Transformations

ChemInform Abstract: New Transformations from a 3-Silyloxy 2-Aza-1,3-diene: Consecutive Zr-Mediated Retro-Brook Rearrangement and Reactions with Electrophiles.

✍ Vincent Gandon; Philippe Bertus; Jan Szymoniak 📂 Article 📅 2000 🏛 John Wiley and Sons ⚖ 35 KB 👁 1 views

Diels-alder reaction of unactivated 2-az

Diels-alder reaction of unactivated 2-aza-1,3-dienes with diethyl ketomalonate: A carbon dioxide equivalent

✍ José Barluenga; Francisco J. González; Santos Fustero 📂 Article 📅 1989 🏛 Elsevier Science 🌐 French ⚖ 252 KB

The [4+2] cycloaddition reaction of diethyl ketomalonate and butyl glyoxalate with unactivatcd 2-aza-1,3-dienes 1 is described for the first time. The inability of the carbon dioxide to undergo [4+2] cycloaddition reactions with dienes is well known.t An alternative procedure is the use of diethylke

A Mild and Efficient aza-Diels—Alder Rea

A Mild and Efficient aza-Diels—Alder Reaction of N-Benzhydryl Imines with trans-1-Methoxy-2-methyl-3-trimethylsiloxybuta-1,3-diene Catalyzed by Yb(OTf)3.

✍ Ke Cheng; Lili Lin; Shikui Chen; Xiaoming Feng 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 21 KB 👁 2 views

Regio- and Stereoselective aza-Diels—Ald

Regio- and Stereoselective aza-Diels—Alder Reaction of Ethyl Glyoxylate 4-Methoxyphenylimine with 1,3-Dienes in the Presence of BF3×Et2O. Evidence for a Non-Concerted Mechanism.

✍ M. Jose Alves; Nuno G. Azoia; A. Gil Fortes 📂 Article 📅 2007 🏛 John Wiley and Sons ⚖ 17 KB 👁 2 views

Molecules with Twist Bent Bonds. A Compa

Molecules with Twist Bent Bonds. A Comparison of the Thermal and Transition-Metal-Complex Promoted Rearrangements of st]Derivatives of trans-Bicyclo[4.1.0]hept-3-ene

✍ Paul G. Gassman; Kata Mlinarić-Majerski 📂 Article 📅 1988 🏛 Elsevier Science 🌐 French ⚖ 239 KB

7-Methyl-frans-bicyclo[4LO]hept-3-ene has been synthesized and the thermal and transitionmetal-complex promoted rearrangements of trans-bicyclo[4.1.0]hept-3-ene, 7-methyl-franr-bicyclo[4.1.0]-hept3-ene, and 7,7-dimethyl-tranr-bicyclo[4.l.O]hept-3-ene have been compared.