| | 1 | Author
| Z. Naturforsch | Requires cookie* | | | Title
| Mechanismus der Cyclotrimerisierung von Phenylvinylketonen und die Kristallstrukturen von 1-((1R*,2S*,3R*,5S*)-und 1-((1R*,2S*,3R*,5R*)- 3.5-Dibenzoyl-2-hydroxy-2-phenylcyclohexylmethyl)-pyrrolidin-2-on  | | | | Abstract
| T h e M e ch a n ism o f C y c lo trim e risa tio n o f P h e n y lv in y lk e to n e s a n d th e C ry sta l S tru c tu re s o f 1-((1R *,2S*,3R *,5S*)-an d 1 -((1 R * ,2 S * ,3 R * ,5 R *)-3 .5 -D ib e n zo y l-2 -h y d ro x y -2 -p h e n y lcy c lo h e x y lm e th y l)-p y rro lid in -2 -o n H . M ö h rle 3 *, R. W ille3, B. M id d e lh a u v e b, D. M o o tz b, H . W u n d e rlic h 1 5 H errn Prof. Dr. E. R eim ann zu m 60. G ebu rtstag g e w id m e t The cyclotrimerisation of l-phenyl-2-propyn-l-ol (1) with pyrrolidin-2-one (2) to the tri-benzoylcyclohexanes 4 and 5 produced -with modifications of the reaction conditions -the phenylvinylketone adducts 17 and 18 as intermediates and additionally the cyclohexylmethyl-pyrrolidin-2-ones 8 and 9. Obviously the mechanism consists of a primary attack of pyrroli-din-2-onat (2a) to a phenylketone (7) followed by a series of consecutive Michael reactions, which give rise to 4 and 5 as well as to 8 and 9. The latter two have been identified by X-ray crystal structure analyses. They crystallize in the monoclinic space group P2j/c, Z=4, with 8: a = 1786,8(6), b = 636.7(2), c = 2280.9(8) pm,y3 = 102.33(3)°; 9: a = 1119.9(7), b = 1165.1(3), c = 2198.6(5) pm, ß = 118.24(4)°. | | | |
Reference
| Z. Naturforsch. 52b, 859—872 (1997); eingegangen am 16. April 1997 | | | |
Published
| 1997 | | | |
Keywords
| Michael Reaction, Polysubstituted Cyclohexanes, Diastereomeres, Consecutive Reactions, Crystal Structure | | | |
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