Citation: Yang Mingyan, Zhang Xiaoteng, Wang Daoquan, Wang Mingan. Synthesis and Crystal Structure of 2-Phenyl/cyclohexyl Cyclododecane Oxime Derivatives[J]. Chinese Journal of Organic Chemistry, ;2016, 36(2): 399-405. doi: 10.6023/cjoc201509025 shu

Synthesis and Crystal Structure of 2-Phenyl/cyclohexyl Cyclododecane Oxime Derivatives

1.
Department of Applied Chemistry, China Agricultural University, Beijing 100193

Corresponding author: Wang Mingan,
Received Date: 21 September 2015
Available Online: 21 October 2015
Fund Project: 国家自然科学基金(No. 21172254)资助项目. (No. 21172254)

2-Cyclohexylcyclododecanone and 2-phenylcyclododecanone were synthesized via reaction of cyclododecanone with bromocyclohexane and lithium phenide using cyclododecanone as raw material, respectivey. The 1,1'-dihydroxy-1,1'- bicyclododecane was also obtained unexpected. 2-Cyclohexylcyclododecanone oxime and 2-phenylcyclododecanone oxime were prepared by reaction of 2-cyclohexylcyclododecanone and 2-phenylcyclododecanone with hydroxylamine chloride, 3-cyclohexylcyclododecan-1,2-dione monooxime and 3-phenyl-cyclododecan-1,2-dione monooxime were synthesized by reaction of 2-cyclohexylcyclododecanone and 2-phenylcyclododecanone with NaNO₂-HCl system. Their crystals were obtained in the solution and X-ray diffraction analyses were carried out. The results showed that [3333] conformation was took by the cyclododecane ring of 1-phenylcyclododecanol and 1,1'-dihydroxy-1,1'-bicyclododecane, the two substituted groups were at corner position, while 2-cyclohexylcyclododecanone oxime took [3333]-2-one, 3-phenylcyclododecan-1,2-dione monooxime took [4233]-3,4-dione conformation and the substituted groups were at side-exo position in their crystals. The results of quantum mechanics calculation were consistent with those of X-ray diffraction. In the crystal structure of 1,1'-dihydroxy- 1,1'-bicyclododecane, the molecules exhibited unique self-assembly property of complete disc overlapping between two molecular layers in the a-axis direction with intermolecular hydrogen bond.
- cyclododecanone oxime,
- cyclododecan-1,2-dione monooxime,
- [3333] conformation,
- [3333]-2-one,
- [4233]-3,4- dione
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