tuted 2-oxazolines (3) and products of their reaction with the excess of epoxide. We assume that the 1 : 1 addition products (2) are first formed and that these are then converted into the 2,5-disubstituted 2-oxazolines (3) by loss of ethylene sulfide (thiirane) (or its polymers). Depending on the reaction time and the amount of epoxide these products (3) may react further to give 4,6-dioxa-l-azabicyclo[3.3.0]octanes (4). H~C -C H -R~ + \ / 0 60 39-40 47-4e 75-11 56-58/0.2 57-58/0.05 154-160/0.15 77-8010.07 26.2 29.3 27 19.8 1.4651 21.0 [ a ] 1.4663 10.4 1.4539 8.8 1.5364 22.9[ a ] This reaction gave also a 22.3 ?< yield (calculated o n epoxide) of c o m p o u n d ( 4 ) , b.p. 126--127'C/0.3 m:n Hg, ni; 1.4768. However, reaction of 5,6-dihydro-2-phenyl-4H-1,3-thiazine (5) with epoxides proceeded no further than the 1 : 1 adduct (6), as did the reaction of the corresponding 1,3-oxazine[ll. / h a ) , RI . CH,-O-C,H5. m.p. 133--134'C, yield 2 5 . 4 % 16b!, Rl C H 2 -0 -CH?-CH-CHI. b.p. 133-134"C/ 0.02 niin Hg, fly; ~ 1.5786, yield 28.8 ; ;The reactions described above were carried out by heating the components at 140 to 150 "C. The products could be isolated by distillation of the reaction mixture. The structures of the products were proved by elemental analysis, molecularweight determination, and I R spectra.Received: J u n e 7th, 1966
262 IE]Publication de!ayed a t the author's request. G e r m a n version: Angew. Chern. 78,938 (1966) [I] R.