The reaction of sesquiterpene lactone achillin with chlorine in methanol afforded four products, via.. two monochlorides and two dichlorides. One of these monochlorides is an intermediate in the formation of both dichlorides. The structures of the reaction products were established by two-dimensional N M R spectroscopy The structure of one of the products was also established by X-ray diffraction analysis.
l~Novosibirsk Institule of Organic Chemisto'. 57be/'ian BraHch of the Rus~tan Academy ~y'Sciences, 9 pros7~. Akad. Lavrenl'eva, 030000 Novosibirsk. Russtan Federation. Fax: +-7 (383 2) 35 4 752. E-mail: raldugin@ni()ch.nsc./'tl lkc rcaclion of grosstnisin (8c,-hydrox?.achdlin. l) with chlorine in hcl/ZCll,2 4fi'oldcd a nlixttlrc of producls. The less polar product readily crystalliTed :.lt'lcr ctlrOlll;ilogr;!pl';y. Accordin(It) the X-l';iy dil}raclion d;.lla, this pruduct has the structure of I tz, 10lJ-dichloro-I, I(.)-dihydrogrossnli~in. The seCt)lid chlcm~ dcmativc of grossillit, iil. w2., 8[3-chloro:lchilthl, was prcp:-Ii'Cd ill gtW,.l )i"ld b$ lhc rc2;.tctioll o[" kil2lltllC I ~illl PCI 5 ill C't-IC'I~ in lhc. pfc~1211cc, t)l" tlv.
Reaction of Guaianolide Achillin with Chlorine in Methanol. -The reaction of sesquiterpene lactone achillin (I) with chlorine in methanol affords four chlorinated and methoxylated products (III)-(VI). (V) is an intermediate in the formation of both dichlorides (III) and (IV). -(ALEBASTROV, O. V.; RALDUGIN, V. A.; SHAKIROV, M. M.; BAGRYANSKAYA, I. YU.; GATILOV, YU. V.; KULYJASOV, A. T.; ADEKENOV, S. M.; TOLSTIKOV, G. A.; Russ.
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