✦ LIBER ✦

Cyclophanes, XXXV. DNMR, molecular mechanics, and crystal structures of 2,11-dithia[3.3]orthometacyclophane and 2,11-dithia[3.3]orthoparacyclophane

✍ Scribed by Bodwell, Graham J. ;Ernst, Ludger ;Hopf, Henning ;Jones, Peter G. ;McNally, John P. ;Schomburg, Dietmar

Publisher: Wiley (John Wiley & Sons)
Year: 1990
Tongue: English
Weight: 515 KB
Volume: 123
Category: Article
ISSN: 0009-2940
DOI: 10.1002/cber.19901231221

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The syntheses of 2,11‐dithia[3,3]orthometacyclophane (5) and 2,11‐dithia[3,3]orthoparacyclophane (6) by dithiol‐dibromide coupling are described. Whereas the yield of 5 is not significantly affected by the substrate pairing, that of 6 is. Both compounds exhibit a temperature‐dependent ^1^H‐NMR spectrum. An energy barrier of 11.0 ± 0.2 kcal/mol (45.7 ± 0.8 kJ/mol) has been calculated for 5, but that of 6 was too low to be determined. Slightly contrasting results were obtained from two different molecular mechanics programs for the relative energies of the six limiting conformations of 5. Crystal structure determinations of 5 and 6 have been carried out, and the conformational behavior of 5 and 6 in solution and in the solid state is discussed.

📜 SIMILAR VOLUMES

Medium-Sized Cyclophanes, 29. Synthesis

Medium-Sized Cyclophanes, 29. Synthesis and Desulfurization of 2,11-Dithia[3]metacyclo- and 2,11-Dithia[3]paracyclo[3](4,9)pyrenophanes

✍ Yamato, Takehiko ;Miyazawa, Akira ;Tashiro, Masashi 📂 Article 📅 1993 🏛 Wiley (John Wiley & Sons) 🌐 English ⚖ 629 KB

Cyclophanes 1 Benzenopyrenophane, 4,g-bridged 1 Sulfones, pyrolysis of Photodesulfurization [2]Naphthaleno[2]paracyclophane, 1,5-bridged 2,11-Dithia[3]metacyclo-(14 b) and 2,11-dithia[3]paracyclo[3]-extrusion by vapor-phase pyrolysis of the corresponding di-(4,g)pyrenophane (14c) were obtained by th

ChemInform Abstract: Medium-Sized Cyclop

ChemInform Abstract: Medium-Sized Cyclophanes. Part 44. Synthesis and Stereochemical Assignments of 9-Substituted 2,11-Dithia(3.3)metacyclophanes.

✍ T. YAMATO; M. SHIGEKUNI; H. KUNUGIDA; Y. NAGANO 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 28 KB 👁 1 views

Alternative General Synthetic Routes to

Alternative General Synthetic Routes to [2.2]Cyclophanes and [3.2]Cyclophanes from [3.3]Cyclophane-2,11-diones by Photodecarbonylation, and a Structural Study of [3.2]Metacyclophanes

✍ Hajime Isaji; Mikio Yasutake; Hiroyuki Takemura; Katsuya Sako; Hitoshi Tatemitsu 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 748 KB

Silver(I) Coordination Polymers of 2,11-

Silver(I) Coordination Polymers of 2,11-Dithia[3.3]paracyclophane and in situ Silver(I) Perfluoro-dicarboxylates

✍ Shuqin LIU; Xiongfu ZHANG; Huilong WANG; Changgong MENG; Wensheng MOU 📂 Article 📅 2009 🏛 John Wiley and Sons 🌐 English ⚖ 206 KB

Crystal and molecular structure of newly

Crystal and molecular structure of newly synthesized 2,3,2′,3′-Bis{8″,11″-dioxa[4.3.3]propella(3″,4″)}biphenyl

✍ Grochowski, Jacek ;Jamrozik, Janusz ;Serda, Paweł ;Zesławski, Wojciech 📂 Article 📅 1995 🏛 John Wiley and Sons 🌐 English ⚖ 249 KB

## Abstract The title compound 5 was obtained from 2,2′,3,3′‐tetramethylbiphenyl in a multi‐step reaction sequence leading to the bis(propellane). X‐ray structure analysis proved the identity of bis(propellane). In the solid state the molecule possesses roughly a twofold symmetry axis perpendicular

ChemInform Abstract: Conformational Anal

ChemInform Abstract: Conformational Analysis of [3.3]Cyclophanes. Part 6. Alternative General Synthetic Routes of [2.2]Cyclophanes and [3.2]Cyclophanes from [3.3]Cyclophane-2,11-diones by Photodecarbonylation, and a Structural Study of [3.2]Metacyclophanes.

✍ Hajime Isaji; Mikio Yasutake; Hiroyuki Takemura; Katsuya Sako; Hitoshi Tatemitsu 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 26 KB 👁 2 views