Acid-catalyzed transformation of rubrene to indenonaphthacene and its paired interacting orbital (PIO) analysis

Tetrahedron Letters

Volumn 44, Issue 6, 2003, Pages 1175-1177

  Hosokawa, Takahiro ^a   Nakano, Hiromi ^a   Takami, Kazuto ^a   Kobiro, Kazuya ^a   Shiga, Akinobu ^b  

^a KOCHI UNIVERSITY OF TECHNOLOGY   (Japan)

^b SUMITOMO CHEMICAL CO LTD   (Japan)

Author keywords

Indenonaphthacene; Paired interacting orbitals; Rearrangement; Rubrene

Indexed keywords

4B,9,10 TRIPHENYL 4B,9 DIHYDROINDENO[1,2,3 FG]NAPHTHACENE; 5,6,11,12 TETRAPHENYLNAPHTHACENE; ALKENE DERIVATIVE; DICHLOROMETHANE; NAPHTHACENE DERIVATIVE; RUBRENE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BINDING; CRYSTAL STRUCTURE; CRYSTALLIZATION; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0037415460     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02831-9     Document Type: Article

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7. +). The yield was determined by NMR.
8. 1 and Rw factors were 0.065 for I>2.0σ(I) data, and 0.243 for all unique reflections, respectively.
9. +] has only one orbital, only one PIO, namely PIO-1, is constructed. The PIO-1 contains all orbital interactions corresponding to electron delocalization interaction and overlap repulsion. Both of the interactions, that is, in-phase interaction and out of phase interaction are graphically illustrated in Figure 2(a), whereas only the repulsive out of phase interaction can be seen in Figure 2(b). Thus, construction of PIOs allows us to easily extract all interactions which are spread over canonical MOs. The PIO analysis presented here was done by using a software called 'LUMMOX™' (Least Unified Meta-Molecular Orbital Calculation System) recently developed by Sumitomo Chemical Co., Ltd in Japan.