Dramatic effects of boryl substituents on thermal ring-closing reaction of vinylallenes

Journal of the American Chemical Society
Masahiro MurakamiTakanori Matsuda

Abstract

The unidirectional thermal ring-closing reaction of cis-4-phenyl-5-borylpenta-1,2,4-triene giving 4-boryl-3-methylene-1-phenylcyclobutene proceeded significantly faster than that of the trans-isomer. The large rate difference between the cis- and trans-stereoisomers is ascribed to electronic participation of the vacant boron p orbital in the transition state SHOMO.

Citations

Aug 7, 2010·Journal of the American Chemical Society·Matthew R SiebertDean J Tantillo
Jan 10, 2009·Journal of the American Chemical Society·Yong LiangJiaxi Xu
May 27, 2010·Beilstein Journal of Organic Chemistry·Kay M Brummond, Joshua M Osbourn
May 26, 2017·Chemistry, an Asian Journal·Naoki IshidaMasahiro Murakami
Sep 12, 2017·Chemical Communications : Chem Comm·Songsong Gao, Xiangdong Hu
Dec 15, 2006·Angewandte Chemie·Jun Hee Lee, F Dean Toste
Oct 22, 2005·The Journal of Organic Chemistry·Zhenfeng XiTamotsu Takahashi

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