98230-16-1

Upstream product

• 102402-94-8 3,6-Bis-methylsulfanyl-2a,3,3a,5a,6,6a,6b,6c-octahydro-dicyclopenta[cd,gh]pentalene-3,6-dicarboxylic acid 
• 102402-92-6 dimethyl exo,exo-5,12-bis(methylthio)tetracyclo<7.2.1.0^4,11.0^6,10>dodeca-2,7-diene-5,12-dicarboxylate 
• 98230-14-9 hexacyclo<5.4.1.0^2.6.0^3.10.0^5.9.0^8.11>dodecane-4,12-dione 

Downstream Products

• 114533-18-5 Toluene-4-sulfonic acid 6-hydroxy-2a,3,3a,5a,6,6a,6b,6c-octahydro-dicyclopenta[cd,gh]pentalen-3-yl ester 
• 114533-17-4 C₂₆H₂₆O₆S₂ 
• 114533-21-0 Toluene-4-sulfonic acid 6-phenylselanyl-2a,3,3a,5a,6,6a,6b,6c-octahydro-dicyclopenta[cd,gh]pentalen-3-yl ester 
• 114533-20-9 3,6-Bis-phenylselanyl-2a,3,3a,5a,6,6a,6b,6c-octahydro-dicyclopenta[cd,gh]pentalene 
• 114533-15-2 C₂₆H₂₆N₄O₄S₂ 

Relevant academic research and scientific papers

Design of a Key Synthon for Dodecahedrane: (C2v)-C12-Tetraquinanedione

A six-step synthesis of tetracyclo4,11.06,10>dodeca-2,7-diene-5,12-dione (2) from the readily available starting materials 7-t-butoxynorbornadiene and 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene is described.

Crystallographic analysis of structural effects associated with symmetrical-1,3-bridging of five-membered rings by carbonyl spacers

The crystal and molecular structures of tricyclo[7.2.1.03,6]decane-2, 8-dione (4), its 4,5-benzo fused homologue (5), and tetracyclo[7.2.1.04,11-.06,10]-dodeca-2, 7-diene-5,12-dione (6) have been determined. The conformations adopted by the saturated and unsaturated five-membered rings In these molecules have been determined. The significantly different angles adopted by the carbonyl groups of the central ring in each of these diketones were also accurately measured. In order to evaluate these relationships, a companion MM2-based computational study was undertaken simultaneously and relevant comparisons are made. The range covered by this triad of molecules provides Insight into structural factors that contribute to the preferred ground-state conformations of bridged diquinane systems.

Studies towards Functionalized/Annulated acs-Tetracyclo4,11.06,10>dodeca-2,7-diene Skeletons - X-ray Structural Analyses of a "face-to-face" Dibenzo Compound and a Tetraoxadihydropagodane

Hexacyclo2,6.03,10.04,8.09,12>dodecane-5,11-dione (15), which is efficiently available from 7-acetoxynorbornadiene (1) and tetrachlorocyclopentadienone dimethyl acetal, is the key substance for the synthesis of hexacyclo2,7.03,11.04,9.010,14>tetradeca-5,12-diene (24) as well as of various 5,12-functionalized acs-tetracyclo4,11.06,10>dodeca-2,7-dienes (32, 36, 40, 41), of some related 2,3-benzo- (84, 85) and "face-to-face" 2,3:7,8-dibenzo compounds (54 - 58), which are sought as photosubstrates.The two isomeric "face-to-face" dipyridazines 65/68 are obtained starting from a pagodane intermediate (60) via the tetraformyl derivative 63.X-ray structural analyses together with MM2 calculations for the dibenzo compound 54 and for the tetraoxadihydropagodane 64 (a peristylane) derived from 63, provide detailed structural informations.

Synthesis of Hexacyclo2,6.0.3,10.04,8.09,12>dodecane-5,11-dione and its Conversion to Di-, Tri-, and Tetranitro-1,3-bishomopentaprismanes

Sulfenylation of the dianion of dimethyl tetracyclo4,11.06,10>dodeca-2,7-diene-5,12-dicarboxylate (9) with dimethyl disulfide delivered the exo,exo-bis(methylthio) derivative 10a.Subsequent saponification and oxidative decarboxylation resulted in transformation to tetracyclo4,11.06,10>dodeca-2,7-diene-5,12-dione (4).Upon photolysis of the bisketal 11 of this pivotal intermediate, arrival at the doubly functionalized 1,3-bishomopentaprismane 12 was achieved.Following acidic hydrolysis to give the title compound 5, elaboration of three dinitro (14 - 16), two trinitro (20, 21), and a tetranitro derivative (22) was accomplished.The configurational assignment to the first four products was achieved by means of 1H NMR spectroscopy and an X-ray crystal structure analysis of 21.The stereochemistries of the nitro-substituted cage molecules are discussed in terms of the mechanism of their formation and their densities, many of which are markedly enhanced.The structural features of the tetranitro-bishomopentaprismane 22 have also been elucidated by X-ray methods.

SYNTHESIS OF A VERSATILE FUNCTIONALIZED TETRAQUINANE. CONVENIENT ACCESS TO 1,3-BISHOMOPENTAPRISMANEDIONE

The tetracyclic diene dione 1 has been synthesized by a short oxidative decarboxylation route starting with the domino Diels-Alder adduct 2.Photocyclization of the bisketal of 1 was used to arrive expediently at 1,3-bishomopentaprismanedione (7).