Wittig reactions of non-stabilized phosphonium ylides bearing a phosphaheteratriptycene skeleton containing group 14 and 15 elements with benzaldehyde

Abstract

Wittig reactions of non-stabilized phosphonium ylides bearing a phosphaheteratriptycene skeleton containing Group 14 and 15 elements (PhSi, PhGe, PhSn, n-BuSn, P, As, Sb, and Bi) at another bridgehead position with benzaldehyde provided (Z)-olefins as a major product in the cases of period 3 elements (PhSi, P) and (E)-olefins as a major product in the cases of below period 4 elements (PhGe, PhSn, n-BuSn, As, Sb, and Bi). These results are attributed to stereochemical drift of the intermediates come from the heteroatom effect at another bridgehead position of the phosphaheteratriptycene skeleton.

GRAPHICAL ABSTRACT

Keywords:

• Wittig reaction
• non-stabilized phosphonium ylide
• phosphaheteratriptycene
• 1,2-oxaphosphetane
• heteroatom effect

Acknowledgment

The authors thank Emeritus Prof. Takayuki Kawashima for useful advices.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This study was partially supported by a Grant-in-Aid for Encouragement of Young Scientists (B) to Y. U. (No.16750041 and No.18750037) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan and Kitasato University Research Grant for Young Researchers.