✦ LIBER ✦

Thermal [2 + 2] cycloaddition of (z)-[6]paracycloph-3-ene with tetracyanoethylene

✍ Scribed by Yoshito Tobe; Tadahiro Sorori; Kazuya Kobiro; Kiyomi Kakiuchi; Yoshinobu Odaira

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 422 KB
Volume: 9
Category: Article
ISSN: 0894-3230
DOI: 10.1002/(sici)1099-1395(199601)9:1<1::aid-poc746>3.0.co;2-1

No coin nor oath required. For personal study only.

✦ Synopsis

Reaction of (Z)-[6]paracycloph-3-ene (2) with tetracyanoethylene (TCNE) gave a [2 + 21 cycloadduct (4, which represents the first example of thermal [ 2 + 2 ] cycloaddition of a benzene derivative under mild conditions. The structure of 4 was confirmed by x-ray crystallographic analysis. Semi-empirical PM3 calculations and the measurement of the He I photoelectron spectrum of 2 indicated that the ionization potential of 2 is considerably lower than that of [6]paracyclophane ( I ) , which gave a [4 + 21 cycloadduct (3)

with TCNE. The unusual pericyclic selectivity and regioselectivity are discussed on the basis of PM3 calculations. The regioselectivity is ascribed to the higher x bond order of the bridgehead aromatic bond of 2, which is on the same side of the bridge double bond, than that o f the bond on the opposite side of the bridge double bond.

📜 SIMILAR VOLUMES

Isomer Formation in the Cycloaddition Re

Isomer Formation in the Cycloaddition Reaction of 2,7-Dimethyl-2,4,6-octatriene with Tetracyanoethylene

✍ Dr. Alden D. Josey 📂 Article 📅 1981 🏛 John Wiley and Sons 🌐 English ⚖ 252 KB 👁 2 views

and references cited therein. [I 11 One route to (E)-I-lithio-I-alkenes which circumvents the (Q-I-halo-Ialkenes is the reaction of (E)-I-tri-n-butylstannyl-I-alkenes with n-butyllithium described by E.

Cobalt(I)-Catalyzed [6 + 2] Cycloadditio

Cobalt(I)-Catalyzed [6 + 2] Cycloadditions of Cyclooctatetra(tri)ene with Alkynes.

✍ Mathieu Achard; Marc Mosrin; Alphonse Tenaglia; Gerard Buono 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 33 KB

Gold-Catalyzed Intramolecular [3+2] Cycl

Gold-Catalyzed Intramolecular [3+2] Cycloadditions of 1-Aryl-1-allene-6-enes

✍ Rupsha Chaudhuri; Hsin-Yi Liao; Rai-Shung Liu 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 English ⚖ 291 KB 👁 1 views

Reaction of Tetracyanoethylene with Alde

Reaction of Tetracyanoethylene with Aldehydes. Synthesis of 6-Imino-2,7-dioxabicyclo[3.2.1]octane-4,4,5-tricarbonitriles.

✍ A. V. Eremkin; O. V. Ershov; S. N. Mol'kov; V. P. Sheverdov; O. E. Nasakin; Ya. 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 18 KB

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

ChemInform Abstract: Reduction of 3-(2-H

ChemInform Abstract: Reduction of 3-(2-Hydroxyethyl)-1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene.

✍ N. N. Yarmukhamedov; N. Z. Baibulatova; T. V. Khakimova; L. V. Spirikhin; V. A. 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 28 KB

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

[4 + 2] Cycloaddition of 2-Substituted 1

[4 + 2] Cycloaddition of 2-Substituted 1,2-Dihydropyridines with Nitrosobenzene: Asymmetric Synthesis of trans-2-Substituted 3-Amino-1,2,3,6-tetrahydropyridines.

✍ Alexandre Lemire; Daniel Beaudoin; Michel Grenon; Andre B. Charette 📂 Article 📅 2005 🏛 John Wiley and Sons ⚖ 20 KB