✦ LIBER ✦

Anti/syn-selectivities in the addition of electrophiles to 8-methylene-endo-tricyclo[3.2.1.0.2,4]octane

✍ Scribed by Reinhard W. Hoffman; Norbert Hauel

Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 186 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)86761-7

No coin nor oath required. For personal study only.

✦ Synopsis

The addition of a variety of electrophiles to the semicyclic double bond of 1 and 4 has been studied. The anti/syn-product ratios show that the=inter&ztion between the Walsh-and n-orbitals causes only small selectivities. Photoelectron spectra revealed a sizeable (H.. = -0.338) through space interaction between the es Walsh orbital of the &opropane ring in 1 with the semicyclic double bond 1) . The molecule can relieve this destabilizing interaction zation double by both polarisation of the semicyclic double bond 2) and by rehybridiat C-83' resulting in "orbital distortion" 4) of the semicyclic bond, cf. as.

📜 SIMILAR VOLUMES

Novel regiospecificity in the acid-catal

Novel regiospecificity in the acid-catalyzed addition of acetic acid to endo-tricyclo[3.2.1.02,4]oct-6-ene

✍ M.A. Battiste; J.M. Coxon; R. Edelman 📂 Article 📅 1972 🏛 Elsevier Science 🌐 French ⚖ 170 KB

We report a striking example of unprecedented regiospecificity in the addition of acetic acid to endo-tricyclo[3.2.1.0z"]oct-6-ene (1). The addition proceeds with surprising ease in acetic acid at 80' (3 days) or at room temperature in the presence of catalytic amounts of toluenesulphonic acid to yi

Synthesis and reactivity of the endo-tri

Synthesis and reactivity of the endo-tricyclo[4.2.0.02,8]oct-3-en-7-yl system; a δ route to the bicyclo[3.2.1]-octa-2,6-dien-8-yl cation

✍ G.W. Klumpp; G. Ellen; J.J. Vrielink 📂 Article 📅 1974 🏛 Elsevier Science 🌐 French ⚖ 183 KB

Furthsr studies of ionizations of endo-bicyclo[2.l.O]pent-2-yl msnts on the nature of the various transition states involved:

ChemInform Abstract: Effect of the Aryl

ChemInform Abstract: Effect of the Aryl Group Substituent in the Dimerization of 3-Arylisoxazoles to syn-2,6-Diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones Induced by LDA.

✍ Leonardo Di Nunno; Paola Vitale; Antonio Scilimati 📂 Article 📅 2009 🏛 John Wiley and Sons ⚖ 33 KB 👁 2 views

## 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 of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v

Nucleophilic Addition to C,C-Double Bond

Nucleophilic Addition to C,C-Double Bonds. Part VIII. The standard enthalpies of formation of anti9,10-10endo-hydroxytricyclo [4.2.1.12,5]deca-3,7-dien-9-one and 9-Oxatetracyclo [5.4.0.03,10.04,8]undec-5-en-2-one and kinetic data for the cyclization of the olefinic alcohol to the ether

✍ Alan A. Smeaton; William V. Steele; Gerardo M. Ramos Tombo; Camille Ganter 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 258 KB 👁 2 views

## Abstract In view of the significance of steric compression in the base‐catalyzed intramolecular cyclization of polycyclic olefinic alcohols, the standard enthalpies of formation of __anti__^9,10^‐10 __endo__‐hydroxytricyclo [4.2.1.1^2,5^]deca‐3,7‐dien‐9‐one **(1)** and 9‐oxatetracyclo [5.4.0.0^3