Interactions and chemistry of 1,8-bis(phenylethynyl)naphthalene and 1,8-bis(1-alkynyl)naphthalenes

Oligosaccharide Analogues of Polysaccharides, Part 19, Synthesis of 2-(Naphthalen-1-yl)ethyl Cellooligoglycosides and [(Naphthalene-1,8-diyl)di(ethane-2,1-diyl)] Bis[cellooligoglycosides]

“…The resulting suspension was stirred for 1 h, treated with BnBr (1.9 ml, 15.9 mmol), and stirred for 4 h, cooled to À 308, treated with MeOH (10 ml), warmed to r.t., and stirred for 0.5 h. After evaporation under high vacuum ( T`408), the residue was diluted with Et 2 O. Workup and FC (hexane/AcOEt 8 : 2) gave 25 3066w, 3015m, 2872m, 1951w, 1810w, 1605w, 1497w, 1454m, 1397w, 1361m, 1310w, 1248w, 1089s, 1072s, 1228m, 1001m, 914w, 832w. (26). At 08, 1m HCl in Et 2 O (ca.…”

“…Cross-coupling of the diiodide 6 [26] with the octynitol 5 [27] gave 39% of the dialkyne 7, besides 5% of the corresponding monoalkynylated monoiodide (Scheme 1) 4 ). However, in view of the low stability of 7 (it decomposed at 238 within a few days), we quickly abandoned this type of compounds.…”

Photoelimination from a γ-substituted α,β-unsaturated ketone

“…The structure of 10 was further substantiated by the similarity of its ultraviolet spectrum to that of benzo(j)fluoranthene (8) and by the expected bathochromic shift of the ultraviolet spectrum on going from neutral to basic medium.…”

Synthesis, Structures, and Physical Properties of Benzo[k]fluoranthene‐Based Linear Acenes

“…[17] The cyclopentadienone derivatives 10 are generated either through the Knoevenagel condensation from acenaphthenequinone and a ketone [18] or by the metal-catalyzed carbonylation of diynes 8. [19] The former method cannot be employed with simple ketones such as acetone or butan-2-one [17] or with ketones that contain acid-or base-sensitive functional groups. The metal-catalyzed carbonylation of diynes 8 can more readily be performed when bulky silyl substituents are present as the R moieties.…”

“…The metal-catalyzed carbonylation of diynes 8 can more readily be performed when bulky silyl substituents are present as the R moieties. [19] Fluoranthenes can be prepared through Rh I -catalyzed [(2+2)+2] cycloadditions between 1,8-diethynylnaphthalenes 8 (Scheme 1) and norbornadiene or a molecule of an alkyne. [20] Similarly, the replacement of an alkyne with a benzyne derivative in this reaction should yield a benzo[k]-fluoranthene 4.…”