Diastereoselective Reformatsky reaction of methyl 4-bromocrotonate with 1,2:5,6-di-O-isopropylidene-α-d-ribo-hexofuranos-3-ulose: application to novel bicyclic nucleosides

This paper describes an efficient synthetic route for novel bicyclic nucleosides. The stereochemistry of the targeted bicyclic nucleosides was successfully achieved by vinylogous Reformatsky reaction and ring closing metathesis reaction on a carbohydrate backbone.     

Comparison of Stereoselectivity of Intramolecular Cyclization of Aldehydes Tethered with Conjugated Esters Induced by O-Stannyl and O-Samarium Ketyls to Form the Tetrahydrofuran Ring Systems

Several (E)- and (Z)-ω-formyl-5-oxa-2-substituted-α,β-unsaturated esters ( 6Za-6Zc; 6Ea-6Ec; 6Eb′-6Ec′; 6Zb′-6Zc′ ) were prepared in high yields. They were subjected to cyclization of their intramolecular ketyl radicals induced by either samarium(II) iodide or tributyltin hydride. These two reagents gave distinct stereoselectivities. More bicylic lactone than monocyclic hydroxy-ester was formed when tributyltin hydride was used, but the opposite stereoselectivity was obtained when samarium(II) iodide was used. The effect of double-bond configuration, heteroatom and substituent on stereoselectivity is described.     

Sharp bounds of the zeroth-order general Randi? index of bicyclic graphs with given pendent vertices

Let G be a simple connected graph and α be a given real number. The zeroth-order general Randi? index of ⁰R_α(G) is defined as ∑_v∈V(G)[d_G(v)]^α, where d_G(v) denotes the degree of the vertex v of G. In this paper, for any α(≠0,1), we give sharp bounds of the zeroth-order general Randi? index ⁰R_α of all bicyclic graphs with n vertices and k pendent vertices.     

Free Pairs of Bicyclic Units in the Integral Group Ring of the Dihedral Group

Hirano studied the quasi-Armendariz property of rings, and then this concept was generalized by some authors, defining quasi-Armendariz property for skew polynomial rings and monoid rings. In this article, we consider unified approach to the quasi-Armendariz property of skew power series rings and skew polynomial rings by considering the quasi-Armendariz condition in mixed extension ring [R; I][x; σ], introducing the concept of so-called (σ, I)-quasi Armendariz ring, where R is an associative ring equipped with an endomorphism σ and I is an σ-stable ideal of R. We study the ring-theoretical properties of (σ, I)-quasi Armendariz rings, and we obtain various necessary or sufficient conditions for a ring to be (σ, I)-quasi Armendariz. Constructing various examples, we classify how the (σ, I)-quasi Armendariz property behaves under various ring extensions. Furthermore, we show that a number of interesting properties of an (σ, I)-quasi Armendariz ring R such as reflexive and quasi-Baer property transfer to its mixed extension ring and vice versa. In this way, we extend the well-known results about quasi-Armendariz property in ordinary polynomial rings and skew polynomial rings for this class of mixed extensions. We pay also a particular attention to quasi-Gaussian rings.     

Characteristics of bicyclic sesquiterpanes in crude oils and petroleum products

This study presents a quantitative gas chromatography–mass spectrometry analysis of bicyclic sesquiterpanes (BSs) in numerous crude oils and refined petroleum products including light and mid-range distillate fuels, residual fuels, and lubricating oils collected from various sources. Ten commonly recognized bicyclic sesquiterpanes were determined in all the studied crude oils and diesel range fuels with principal dominance of BS3 (C₁₅H₂₈), BS5 (C₁₅H₂₈) and BS10 (C₁₆H₃₀), while they were generally not detected or in trace in light fuel oils like gasoline and kerosene and most lubricating oils. Laboratory distillation of crude oils demonstrated that sesquiterpanes were highly enriched in the medium distillation fractions of ∼180 to 481 °C and were generally absent or very low in the light distillation fraction (boiling point to ∼180 °C) and the heavy residual fraction (>481 °C). The effect of evaporative weathering on a series of diagnostic ratios of sesquiterpanes, n-alkanes, and biomarkers was evaluated with two suites of weathered oil samples. The change of abundance of sesquiterpanes was used to determine the extent of weathering of artificially evaporated crude oils and diesel. In addition to the pentacyclic biomarker C₂₉ and C₃₀ αβ-hopane, C₁₅ and C₁₆ sesquiterpanes might be alternative internal marker compounds to provide a direct way to estimate the depletion of oils, particularly diesels, in oil spill investigations. These findings may offer potential applications for both oil identification and oil-source correlation in cases where the tri- to pentacyclic biomarkers are absent due to refining or environmental weathering of oils.     

Aza-annulation of β-enaminolactones: application to the synthesis of enantiopure difunctionalized bicyclic lactams

Diastereoselective aza-annulation of seven-membered β-enaminolactones 2 gives access to bicyclic heterocyles 5. Fragmentation of molecule 5a with lithium methoxide affords cis or trans bicyclic lactams 8 with excellent stereoselectivities.     

On the Laplacian coefficients of bicyclic graphs

Let G be a graph of order n and let be the characteristic polynomial of its Laplacian matrix. Generalizing the approach in [D. Stevanovi?, A. Ili?, On the Laplacian coefficients of unicyclic graphs, Linear Algebra and its Applications 430 (2009) 2290-2300.] on graph transformations, we show that among all bicyclic graphs of order n, the kth coefficient c_k is smallest when the graph is B_n (obtained from C₄ by adding one edge connecting two non-adjacent vertices and adding n−4 pendent vertices attached to the vertex of degree 3).     

Production of enantiopure β-amino-γ-hydroxyesters from benzoic acid by a selective formal aminohydroxylation

The enantioselective preparation of three protected β-amino-γ-hydroxyesters from benzoic acid is described. The employed synthetic methodology involves the ipso, ortho cis-dihydroxylation of benzoic acid by the mutant strain Ralstonia eutropha B9, followed by a selective halonium induced beta lactamization. Modification of this novel β-lactam structure by the appropriate sequence of reactions allows for the selective preparation of the aforementioned β-amino-γ-hydroxyesters in a diastereodivergent manner. The overall transformation results in a selective formal aminohydroxylation of the diene moiety of the initial cis-cyclohexadienediol. The synthesized products are important building blocks and will allow for the selective preparation of aminoacids, inosamines and alkaloids from benzoic acid.     

[(HBNPEt3)4NPEt3]3+ – ein bicyclisches Penta(phosphorano)boraziniumTrikation

[(HBNPEt₃)₄NPEt₃]³⁺ – a Bicyclic Penta(phosphorano)borazinium Trication [(HBNPEt₃)₄NPEt₃]Br₃ ( 1 ) has been prepared by the reaction of Me₃SiNPEt₃ with [HBBr₂(SMe₂)] in dichloromethane solution at 20°C. According to ¹¹B‐NMR and ³¹P‐NMR spectroscopy and to a crystal structure determination the cation of 1 has the structure of a bicyclic penta(phosphorano)borazinium‐trication. 1 _.3CH₂Cl₂: Space group P2₁2₁2₁, Z = 8, lattice dimensions at –83°C: a = 2124.8(1), b = 2307.6(1), c = 2323,1(1) pm, R₁ = 0.0733.