67498-38-8Relevant articles and documents
A reactive lactonic dienophile - 3-carbethoxy-5,5-dimethyl-2(5H)-furanone. Application to the synthesis of a monoterpenoid lactone
Liu, Hsing-Jang,Browne, Eric N. C.,Pednekar, Purushottam R.
, p. 921 - 925 (1982)
In contrast to the low dienophilicity generally observed for α,β-unsaturated lactones, the title compound 2 is shown to be a reactive dienophile.Under stannic chloride catalysis, it undergoes Diels-Alder reaction regio- and stereoselectively with a variety of dienes at room temperature.The synthesis of (+/-)-o-mentha-1,3-dien-1->8-olide (20) has been achieved by a two-step sequence using lactone ester 2.Addition of 2 to 1-acetoxy-1,3-butadiene afforded epimeric acetoxy lactones 12 and 13 which were converted to the monoterpenoid lactone 20 by treatment with lithium iodide dihydrate in collidine.
REFORMATSKY REACTION WITH DIETHYL 2-(2-CHLORO-2-METHYLPROPYLIDENE)MALONATE. ANALYSIS OF THE PRODUCTS BY PMR SPECTROSCOPY
Shchepin, V. V.,Rodygin, A. S.,Balandina, M. I.
, p. 1798 - 1801 (2007/10/02)
The reaction of diethyl 2-(2-chloro-2-methylpropylidene)malonate with zinc gives an ambident organozinc compound.With electrophilic reagents the latter gives the products from γ and α attack, i.e., derivatives of alkylidene- and alkenylmalonic acid with a preference for the latter.
