73442-10-1Relevant articles and documents
Synthesis with α-Metalated Isocyanides, XLIII. - Experiments with Lithiated α,ω-Alkylene Diisocyanides
Stafforst, Diethart,Schoellkopf, Ulrich
, p. 28 - 36 (2007/10/02)
1,2-Ethylene diisocyanide (4a) reacts with two equivalents of butyllithium (-100 deg C) to give 1,1-dilithio-1,2-ethylene diisocyanide (7) which with ketones yields the oxazines 11. - 1,3-Propylene diisocyanide (4b) reacts with one equivalent butyllithium (-70 deg C) to furnish 1-lithio-1,3-propylene diisocyanide (12) which cyclizes to afford 3-lithio-1-pyrrolin-3-yl isocyanide (14).With ketones, chlorotrimethylsilane, and epoxides 14 furnishes the compounds 17-19 and 21. - 1,4-Butylene diisocyanide (4c) reacts (-100 deg C) with one equivalent butyllithium to give 1-lithio-1,4-butylene diisocyanide (23), and with two equivalents to give 1,4-dilithio-1,4-butylene diisocyanide (28).Both compounds are thermolabile, but can be trapped by electrophils which react below -60 deg C.