Cyclobutanone cyanohydrin

Cyclopropanone and cyclobutanone cyanohydrins. Stork has extended his synthesis of ketones from protected cyanohydrins of aldehydes (equation I) to a synthesis of cyclic ketones, in particular, cyclopropanone and cyclobu-... 

Cyclobutanone cyanohydrin (8) was prepared in the same way from the protected cyanohydrin of 4-chlorobutyraldehyde (6). Treatment of (8) in pentane with 1 N sodium hydroxide solution saturated with sodium chloride for 5 min. 

Cyclobutanedicarboxylic acid, 546 Cyclobutanes, 334-335 Cyclobutanone, 391, 620 Cyclobutanone cyanohydrin, 530 Cyclobutanone dimethyl dithioacetal... 

Cyclobutanone cyanohydrin in ether added slowly at 0° under Ng to phenyl-magnesium bromide in anhydrous ether, warmed to room temp., and stirred 2 hrs. 2-amino-2-phenylcyclopentanone. Y 75%. F. e., also cyclopentan-2-olones, s. J. d Angelo, Bl. 1975, 333. 

Exercise 16-12 Explain what factors would operate to make the equilibrium constant for cyanohydrin formation 1000 times greater for cyclohexanone than for cyclo-pentanone. Why What would you expect for cyclobutanone relative to cyclopenta-none Why ... 

Cyclopropane cyanohydrin (83) has been synthesized by the cyclodehydrohalogenation of protected chloropropionaldehyde cyanohydrin (80) (Scheme 33). The protected cyanohydrin (81) is converted in two steps to cyclobutanone (82). ... 

It is well known that cyclobutanones can be transformed to cyclopentane derivatives directly with diazomethane or indirectly via the cyanohydrins or with tris(phe-... 

The protected cyclopropanone cyanohydrin (15) has been converted into cyclobutanone, which can also be obtained by an identical route from 4-chlorobutanal. Tricyclo[3,2,0,0 ]heptan-6-ones have beat implicated as reaction intermediates in... 

Cyanides, ion 284, 287 Cyano complexes 297, 309, 312 Cyanohydrins 84 Cyanurates 88. 146, 177 Cyanuric acid 177 Cyclo-ociadiene 306 Cyclo-olefines 72 Cycloalkanes 23, 35, 44, 54 Cyclobutanes 23, 55 Cyclobutanones 26, 120 Cyclobutene 1,2-diones 73, 316 Cyclobutenes 72 Cyclohexenes 72 Cyclopentadienes 76, 296, 308 Cyclopentanone 116 Cyclopentenes 26, 120 Cyclopropanes 23, 35, 40, 54, 255 Cyclopropenes 72 Cyclopropenone complexes 307 Cyclopropyl ketones 121... 

Analogues of established carbonyl equivalents include Et2NCH(CN)Li, which is a useful derivative similar to cyanohydrin-derived carbanions, from which either aldehydes or ketones are derivable. " A similar species may be converted into the new Michael acceptor 2-aminoacrylonitrile. a- Metallated cyclopropyl isocyanides and ketones R R C=0 give (14), which on hydrolysis and acid-induced ring expansion lead to cyclobutanones (15). " Cyclobutanone itself is conveniently prepared from lithiated phenylthiocyclopropane and formaldehyde, followed by ring expansion. ... 

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