262 



REPORTS ON THE STATE OF SCIENCE. 



acids ; hence the addition of the elements of ethyl malonate must have 



C„H, .CH-CH .CH 



\ 



CH,-CO 



CH2-C 



CH (10) 



C„H, . GOGH HOOC . CH 



< 



OH' 



CH, . COOH 



CHj . COOH 



taken place at the a/3 position relative to the carbonyl group. As this 

 addition may be influenced by the tendency to form a six-ring, cinna- 

 menylacrylic acid, CgHs.CH : CH.CH : CH.COOC^Hs, where no ring for- 

 mation is possible, was substituted for cinnamylideneacetone, but again 

 addition took place at the a/3 position. 



Dimethyldihydroresorcin (and also probably phenyldihydroresorcin) 

 gives rise to a crystalline and an amorphous oxime.^ The former can be 

 converted into a dioxime, whereas the latter cannot, nor does it give an 

 acetyl derivative, which makes it appear probable that it has the constitu- 

 tion of a hydroxamic acid. 



(CH3), 





CH„-CO\ 



CH3-C(NH . OH) 



On the other hand, both oximes have faintly acid properties, and may 

 therefore be stereoisomerides. Dimethyldihydroresorcin gives a mono- 

 phenylhydrazone and also a mono-anilide, which behaves in a similar 



(CH,), 



^^CH,-CO\(.jj 

 \cHj-C-NH . C^H, 



manner to the amorphous oxime, in not condensing with a second 

 molecule of aniline to form a di-anilide, nor does it yield an oxime, but it 

 gives an acetyl derivative. The compounds formed by the condensation 

 of dimethyldihydroresorcin with 0- and ^-toluidine and a-naphthylamine 

 are also described. 



Work of a similar nature, but more comprehensive, has been carried 

 out by Haas,2 who shows that dimethyldihydroresorcin (11) condenses with 

 only one molecule of a primary base (ammonia, aniline or ^-toluidine), 

 water being eliminated between the hydroxyl group of the dihydroresorcin 

 and a hydrogen atom of the amino group, to give a compound of the type 

 of formula 12. On the other hand, chloroketodimethyltetrahydrobenzene 

 (13) reacts directly with two molecules of a primary base, yielding a 

 compound of the type of formula 14. 



HjC 



(11) 



(13) 



HO .C 



HjC 



CIC 



C(CH3), 

 /\CH. 



CO 

 CH 



C(CH,), 

 /^CH, 



./\ 



(12) 



R.NH-C 



CH 



.'CO 



(H) 



CH 



CO 



RHN C 



CH 



C = NR 



Gittel, Cent. Blatt, 1896 (1), 33. 



2 J. C. S., 1906, 89, 187. 



