695-28-3

Upstream product

• 33482-80-3 5,5-dimethyl-1,3-cyclohexadiene 
• 1220-79-7 1.1-Dimethyl-cyclohexyl-⁽²⁾-p-toluolsulfonat 
• 90976-02-6 3,3-dimethyl-1,7-octadiene 
• 38077-53-1 3,3-dimethylcyclohexyl 1-tosylate 
• 767-12-4 3,3-dimethylcyclohexanol 
• 17530-69-7 3-chloro-5,5-dimethylcyclohex-2-en-1-one 
• 1193-46-0 2,2-dimethylcyclohexanol 
• 51335-83-2 (1R,3S)-5,5-dimethylcyclohexane-1,3-diol 
• 126-81-8 dimedone 
• 734-26-9 3,3-Dimethyl-cyclohexanon-p-tosylhydrazon 
• 61286-82-6 C₁₅H₂₂N₂O₂S 

Downstream Products

• 94986-33-1 Ir((FC₆H₄)3P)2((CH₃)2C₆H₅)H⁽¹⁺⁾*SbF₆^(1-)=(Ir((FC₆H₄)3P)2(C₆H₅(CH₃)2H))SbF₆ 

Relevant academic research and scientific papers

Radical formation in the oxidation of 2,2′-azo-2-methyl-6-heptene by thianthrene cation radical

Reaction of 2,2′-azo-2-methyl-6-heptene (1) with thianthrene cation radical perchlorate (Th?+ClO4-) in CH2Cl2 solution containing 2,6-di-tert-butyl-4-methylpyridine (DTBMP) gave a mixture of nine C8 hydrocarbons, namely, 1,1,2-trimethylcyclopentane (4, 2.2%), 6-methyl-1-heptene (5, 2.2%), 2-methyl-1,6-heptadiene (6, 9.8%), 2,2-dimethyl-1-methylenecyclopentane (7, 2.9%), 6-methyl-1,5-heptadiene (8, 39%), 3,3-dimethyl- (9, 7.6%), 4,4-dimethyl- (10, 11%), 1,2-dimethyl- (11, 5.4%), and 1,6-dimethylcyclohexene (12, 1.5%). The amounts of acyclic dienes (6, 8) fell and of cyclohexenes (9, 10) rose when DTBMP was omitted from or diminished in the solution. The results provide firm evidence (products 4, 5, and 7) for the formation of the 2-methyl-6-hepten-2-yl radical (2), although the major fate of 2 is its oxidation to the corresponding cation 13, the origin of the bulk of the other products.

Practical catalyst for cyclic metathesis. Synthesis of functional and/or enantiopure cycloalkenes

The oxo-tungsten complex trans-WOCl2(OAr)2 (Ar = 2,6-dibromophenyl) is prepared by reaction of WOCl4 with 2 equiv of 2,6-dibromophenol. A variety of nonconjugated dienes are cleanly cyclized to the corresponding cycloalkenes using 2 mol % of this catalyst in combination with 4 mol % of tetraethyllead. All three components of the catalyst system are commercially available. The catalytic reactions are typically complete in 1 h at 90 °C and allow the synthesis of chiral cycloalkenes with little or no loss in optical activity. For example, (R)-and (5)-citronellene have been cyclized to the corresponding (R)- or (S)-3-methylcyclopentenes in 97% enantiomeric excess. The cyclization is compatible with a variety of functional groups including some ester, amide, and ether derivatives. Tri- (but not tetra-) substituted cycloalkenes could be prepared using this catalyst.

Electro-reductive cleavage of some tosylhydrazones in the presence of oxygen

The superoxide ion induced fragmentation of tosylhydrazones of p-anisaldehyde (1a) 4-(dimethylamino)benzaldehyde (1b), 2-methylcyclohexanone (1c), 2,2-dimethylcyclohexanone (1d), spirodecan-6-one (1e) and 1-indanone (1f) at mercury catode in DMF affords the olefinic products (2a-f) in good yields.