Synthesis and physical properties of several acetylenic hydrocarbons

Abstract

As a part of researches conducted on hydrocarbons a s jet-fuel components under the auspices of the National Advisory Committee for Aeronautics, a number of acetylenic hydrocarbon s and their intermediates have been prepared. The d etails of these syntheses and the physical constants m easured on th e compounds are presented.

Identification of Hydrocarbons by Gas Chromatography.

“…The compounds are listed in order of increasing boiling point in Table I with the source of supply and a literature value for the boiling point (4,11,14,15,17).…”

Polylithium compounds. 8. Synthesis of allenes and acetylenes from perlithiopropyne, trilithiobutyne, and dilithio-3-methylbutyne

“…Dilithiopropargylides which have another hydrogen at carbon atom 3 can undergo further lithiation in Journal of the American Chemical Society / 98:26 / December 22,1976 r/Vlithiated species coincidentally have infrared absorptions at the same frequency as d/lithiated compounds having allenic structures. Further metalation can occur only in the case of propyne resulting in a tetralithio derivative which can be described either as a tetralithiopropargylide, 37, or a tetralithiosesquiacetylene, 38.…”

“…1H NMR (CC14) 0.23 (s): IR (CC14) 2975, 2895, 1880, 1400, 1235, 840-710 (broad) cm-1; mass spectrum m/e (rel intensity) 512 (3), 512 (7), 511 (5), 510 (11), 509 (9), 508 (14), 507 (8), 506 (14), 505 (7), 504 (11), 503 (5), 502 (7), 501 (3), 500 (5), 499 (6). 698 (6), 497 (15), 496 (12), 495 (25), 494 (16), 493 (32), 492 (17), 491 (35), 490 (14), 489 (26), 488 (9), 487 (16), 486 (3), 485 (8), 121 (24), 119 (100), 118 (23), 117 (73), 115 (38), 57 (26), 44 (66), 43 (25), 41 (36), 40 (92). Anal.…”