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. Author manuscript; available in PMC: 2012 Aug 10.
Published in final edited form as: Chem Rev. 2011 Jun 28;111(8):5042–5137. doi: 10.1021/cr100212h

Table 7.

Relative stabilities of alkyne/allene isomers at −20 °C

R X ΔG (allene–alkyne, kcal/mol) experimental alkyne:allene
H Ph −3.7 30:70
H 6-MeO-naphth-2-yl −4.3 20:80
H thiophen-2-yl −3.0 61:39
H N-phthalimido −6.5 6:94