Novel W(CO)<sub>6</sub>‐Promoted C‐S Bond Cleavage Reactions of Dithianes. X‐Ray Structure of 9,9′:9,9′‐Terfluorene

Kuo, Chi-Hong; Lnh, Tien‐Yau; Cheng, Ming‐Chu; Peng, Shie‐Ming

doi:10.1002/jccs.199100006

J Chinese Chemical Soc

1991

DOI: 10.1002/jccs.199100006

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Novel W(CO)₆‐Promoted C‐S Bond Cleavage Reactions of Dithianes. X‐Ray Structure of 9,9′:9,9′‐Terfluorene

Chi-Hong Kuo

Tien‐Yau Lnh

Ming‐Chu Cheng

et al.

Abstract: The reactions of dithianes with W(CO)o in refluxing chlorobenzene give dimeric alkenes and their reduced products; fluorenone derivative yielding trimer 8. A radical mechanism is suggested. The structure of 8 has been determined by a single-crystal X-ray diffraction study. Crystal data: P2 t /n;a == 11.94& (5) 35(1)

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Cited by 7 publications

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“…The dimeric alkene is obtained in low yield and the trimer is isolated as the major product (eq 18). 26…”

mentioning

confidence: 99%

A tribute to Professor Tien-Yau Luh

Lee¹

2023

Arkivoc

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Tien-Yau Luh was born in Wuhan on Mainland China in 1946 immediately after the end of World War II. The civil war in China had just started and the country was in chaos. In January of 1948, his father, a civil engineer, moved the family from Shanghai to Taipei where Dr. Luh grew up in a peaceful atmosphere. He had wanted to study chemistry since the age of sixteen, and was admitted to the National Taiwan University (NTU) in 1963. Inspired by Professor Yau-Tang Lin, his organic chemistry teacher, he was determined to pursue an academic career in this area. After graduation, he spent a year in Professor Lin's laboratory at NTU working on natural product isolation before undertaking the one-year mandatory military service in Taiwan. In 1969, he joined the University of Chicago and in 1974 was awarded his Ph.D. working on physical organic chemistry (with Leon M. Stock). He spent two years at the University of Minnesota as a postdoc studying synthetic methodology and heterocyclic chemistry (with Paul G. Gassman) and in 1976 at the Chinese University of Hong Kong as a lecturer in chemistry. He was promoted to Senior Lecturer in the mid-eighties and returned to his Alma Mater in 1988 as Professor of Chemistry. Throughout the years at NTU, he has held several prestigious professorships such as National Chair and NTU Chair and won numerous awards in Taiwan. From the fall of 2001 to 2004, he was on secondment from the NTU to serve as Director and Distinguished Research Fellow of the Institute of Chemistry, Academia Sinica. He has published over 305 papers and two books, delivered more than 300 research seminars all over the world including the prestigious Schulich Lecture in Technion, Israel, the Yoshida Lecture at Kyoto and Osaka, Japan and JSPS Visiting Professorship. He has served as a member of advisory boards for ChemComm,

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“…The dimeric alkene is obtained in low yield and the trimer is isolated as the major product (eq 18). 26…”

mentioning

confidence: 99%

A tribute to Professor Tien-Yau Luh

Lee¹

2023

Arkivoc

View full text Add to dashboard Cite

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A Variation of Titanium-Induced Carbonyl Coupling – Synthesis and Conformations of Terfluorenyl

Pogodin

Cohen

Agranat³

1999

Eur. J. Org. Chem.

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Reaction of fluorenone (4) with a low‐valent titanium reagent generated from TiCl4 and Zn in THF in the presence of pyridine gave terfluorenyl (6) in 71% yield, bifluorenylidene (2), the conventional McMurry reaction product, in 2% yield, and additional reduction products. The reductive “trimerization” was rationalized in terms of an attack of the intermediate fluorenone dianion on bifluorenylidene. The molecular structure of a single crystal of 6 indicated an approximately C2 conformation, with a slightly twisted central ring, and two equally folded side moieties with dihedral angles of 58.1° and 58.0° between the central and side five‐membered rings. The AM1 and PM3 calculations showed C2 global minima, similar to the conformation in the crystal. The calculated Cs transition state conformations were found to be 21.3 (AM1) and 19.9 (PM3) kcal/mol higher in energy than the global C2 minima. A 2D‐NMR NOESY experiment on 6 supported the C2 (+sc,+sc) or C2 (–sc,–sc) conformation in solution.

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Mild and Efficient Deprotection of 1,3-Dithianes withN,N′- Diiodo-N,N′-1,2-Ethanediyl-Bis(p-Toluenesulphonamide)

Ghorbani‐Vaghei

Zolfigol

2005

Jnl Chinese Chemical Soc

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Novel W(CO)₆‐Promoted C‐S Bond Cleavage Reactions of Dithianes. X‐Ray Structure of 9,9′:9,9′‐Terfluorene

Cited by 7 publications

References 12 publications

A tribute to Professor Tien-Yau Luh

A tribute to Professor Tien-Yau Luh

A Variation of Titanium-Induced Carbonyl Coupling – Synthesis and Conformations of Terfluorenyl

Mild and Efficient Deprotection of 1,3-Dithianes withN,N′- Diiodo-N,N′-1,2-Ethanediyl-Bis(p-Toluenesulphonamide)

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Novel W(CO)6‐Promoted C‐S Bond Cleavage Reactions of Dithianes. X‐Ray Structure of 9,9′:9,9′‐Terfluorene

Cited by 7 publications

References 12 publications

A tribute to Professor Tien-Yau Luh

A tribute to Professor Tien-Yau Luh

A Variation of Titanium-Induced Carbonyl Coupling – Synthesis and Conformations of Terfluorenyl

Mild and Efficient Deprotection of 1,3-Dithianes withN,N′- Diiodo-N,N′-1,2-Ethanediyl-Bis(p-Toluenesulphonamide)

Contact Info

Product

Resources

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Novel W(CO)₆‐Promoted C‐S Bond Cleavage Reactions of Dithianes. X‐Ray Structure of 9,9′:9,9′‐Terfluorene