A nonspectroscopic method to determine the photolytic decomposition pathways of 3-chloro-3-alkyldiazirine: carbene, diazo and rearrangement in excited state

Takatsugu Wakahara; Yasuyuki Niino; Takashi Kato; Yutaka Maeda; Takeshi Akasaka; Michael T H Liu; K Kobayashi; S Nagase

doi:10.1021/ja0116876

A nonspectroscopic method to determine the photolytic decomposition pathways of 3-chloro-3-alkyldiazirine: carbene, diazo and rearrangement in excited state

J Am Chem Soc. 2002 Aug 14;124(32):9465-8. doi: 10.1021/ja0116876.

Authors

Takatsugu Wakahara¹, Yasuyuki Niino, Takashi Kato, Yutaka Maeda, Takeshi Akasaka, Michael T H Liu, K Kobayashi, S Nagase

Affiliation

¹ Contribution from the Center for Tsukuba Advanced Research Alliance, University of Tsukuba, Ibaraki 305-8577, Japan.

PMID: 12167042
DOI: 10.1021/ja0116876

Abstract

C(60) acts as a mechanistic probe for the formation of carbene, diazo compound, and for the rearranged product via the excited state in the photolysis of 3-chloro-3-isopropyldiazirine and 3-chloro-3-chloromethyldiazirine. The carbene adds to C(60) to form methanofullerene, whereas the diazo compound adds to C(60) to form fulleroid. The olefin product arises as a result of the rearrangement in the excited state.