Despite being predicted to be stereoelectronically favorable by the Baldwin rules, efficient formation of a C−C bond through a 5-endo-dig radical cyclization remained unknown for more than 40 years This work reports a remarkable increase in the efficiency of this process upon β-Ts substitution, which led to the development of an expedient approach to densely functionalized cyclic 1,3-dienes Good qualitative agreement between the increased efficiency and stereoselectivity for the 5-endo-dig cyclization of Ts-substituted vinyl radicals and the results of density functional theory analysis further confirms the utility of computational methods in the design of new radical processes Although reactions of Br atoms generated through photochemical Ts−Br bond homolysis lead to the formation of cyclic dibromide side products, the yields of target bromosulfones in the photochemically induced reactions can be increased by recycling the dibromide byproduct into the target bromosulfones through a sequence of additio

In search of efficient 5-endo-dig cyclization of a carbon-centered radical: 40 years from a prediction to another success for the Baldwin rules.

Subduction-related rodingites from East Othris, Greece: Mineral reactions and physicochemical conditions of formation

Geochemical processes and petrogenetic evolution of rodingite dykes in the ophiolite complex of Othrys (Central Greece)

Molecular Solids Formed by the Self‐Organisation of Dialcohols into Hydrogen‐Bonded Ladders

Rh(I)-catalyzed Pauson–Khand reaction of 1-phenylsulfonyl-1,2-octadien-7-yne derivatives

Synthesis of cycloalkadiynes of various ring size

The cyclododecadiynes 3b–d, 8b–d, and 10b–c with functionalities in two propargylic positions, as well as the monofunctionalized diyne 13b have been prepared from simple open-chain building blocks. In the DMPU ( = N,N'-dimethylpropyleneurea)-assisted ring-closing alkylation of 1,7-diynes, the twelve-membered ring compounds have been prepared in yields of 16–55%. The preparation of the diene-diyne 15 and the cyclododeca-5,11-diyne-1,4-dione 18 are described.

Synthesis and Structure of Functionalized Cyclododecadiynes and ‐dienes

Synthesis of some di- and tricyclic silaalkanes

The synthesis of substituted cyclododeca-1,6-diallenes.( = cyclododeca-1,2,6,7-tetraenes) from cyclododeca-5,11-diyne-1,4-diols is described (Schemes 1 and 3). The ca. 1:1 mixtures of the stereoisomers of the cyclododeca-1,6-diallenes were formed in high yields from the ca. 1:1 diastereoisomer mixtures of the 1,4-disubstituted cyclododeca-5,11-diynes by reactions with Me2CuLi or t-BuMgCl/CuII. In mechanistically relevant experiments with the pure diastereoisomers of 1,4-dimethylcyclododeca-5,11-diyne-1,4-diol, it is demonstrated that the configuration is conserved in these reactions. The first synthesis of a 1-substituted cyclododeca-2,8-diyne bearing only one propargylic leaving group gives access to a mixed 12-membered allen-yne (Scheme 5).

Diastereoselective Synthesis of Cyclododeca-1,6-diallenes ( = cyclododeca-l,2,6,7-tetraenes)

Cyclododeca-2,8-diyne-1,10-diol, (6), C 12 H 16 O 2 , and 1,10-dimethylcyclododeca-2,8-diyne-1,10-diol, (11), C 14 H 20 O 2 , have been prepared and their structures determined. Both crystallize in centrosymmetric space groups and the molecules have approximate C2 symmetry. For compound (6), the lengths of the triple bonds are 1.184(3) (C2?C3) and 1.189 (3) A (C8?C9). The bond angles at the triple bonds (C1-C2?C3 and C8?C9-C10) deviate by less than 6° from 180°. For compound (11), the lengths of the triple bonds are 1.190(3) (C2?C3) and 1.188(3)A (C8?C9), and the bond angles at the triple bonds are close to 175.5°. In both compounds, the two 3-hexyne chains maintain a 'crossed' arrangement whereas the two alkylene chains are arranged in a manner similar to that described for unsubstituted cyclododecane.

The First Crystal Structure Analysis of Cyclododeca-2,8-diyne-1,10- diols.

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